Category: 85006-25-3

Electric Literature of 85006-25-3,Some common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Tert-butyl (tert-butoxycarbonyl)oxycarbamate (70 mg) and 1- (bromomethyl) -2-fluorobenzene (56.7 mg) were dissolved in CH 2Cl 2(7 ml) . The mixture was added 1M NaOH (0.33 ml) and tetrabutylammonium bromide(4.83 mg) , and stirred at room temperature for overnight. The resulting mixture was washed with water and dried with Na 2SO 4, concentrated in vacuo and purification by silica gel chromatography to give tert-butyl ( (tert-butoxycarbonyl) oxy) (2-fluorobenzyl) carbamate (82 mg, 80%) . 1HNMR (400 MHz, CDCl 3): delta 7.31-7.37 (m, 4H) , 4.52(s, 2H) , 1.46 (s, 9H) , 1.44 (s, 9H) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (tert-butoxycarbonyl)oxycarbamate, its application will become more common.

Reference:
Patent; SU, Yaning; SIRONAX LTD; ZHANG, Zhiyuan; YANG, Yi; WANG, Guozheng; LIU, Wendong; MA, Yongfen; REN, Yan; (74 pag.)WO2020/103859; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 85006-25-3, A common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 85006-25-3, Computed Properties of C10H19NO5

Commercially available Compound 12 (6.7 g, 28.7 mmol), 2-methoxyethanol (2.267 mL, 28.7 mmol) and triphenylphosphine(9 g, 34.5 mmol) were dissolved in tetrahydrofuran (67 mL) under water-cooling bath, and 2.2 mol/L DEADtoluenesolution (15.67 mL, 34.5 mmol) was added dropwise to the solution over 30 minutes. Then, the reaction mixturewas stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silicagel column chromatography (hexane-ethyl acetate) to give Compound 13 (8.15 g, Yield 97.4%).LC/MS (Method 2) RT = 2.20, MS (m/z) = 292

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shionogi & Co., Ltd.; YUKIMASA, Akira; NAKAMURA, Kenichiroh; INAGAKI, Masanao; KANO, Kazuya; FUJIU, Motohiro; YAMAGUCHI, Hiroki; HATA, Kayoko; INOUE, Takatsugu; (253 pag.)EP3330256; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 85006-25-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of tert-butyl-N-(tert-butoxycarbonyloxy) carbamate (224 mg, 0.96 mmol) in DMF (2 [MNo.) ] was reacted with sodium hydride (38 mg, 0.96 mmol) at [0 C] and stirred for 20 mins at room temperature. The reaction mixture was treated by dropwise addition of benzyl [N- [4- (BROMOMETHYL)-2-FLUOROPHENYL]] carbamate compound 52 (250 mg, 0.74 mmol) and stirred for 1 hour. After concentrating, residual mixture was purified by column chromatography on Silica gel with EtOAc/hexanes (1: 5) solvent mixture as an eluant to give 355 mg of yellow oil of tert-butyl [N-[(TERT-BUTOXYVARBONYL) OXY]-N-{4-] [[(BENZYLOXY) CARBONYLAMINO]-3-FLUOROBENZYL} CARBAMATE] compound 53 (yield: [98%).] 1H-NMR [(CDC13)] 8 : 8.06 (bt, 1 H), 7.35-7. 45 (m, 5 H, Ph), 7.05-7. 12 (m, 2 H), 6.89 (bs, 1 H, NH), 5.22 (s, 2 H, [OCH2PH),] 4.68 (s, 2 H, CH2NO), 1.48 (s, 9 H, C [(CH3)] 3), 1.47 (s, 9 H, [ C (CH3) 3)]

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Digital Biotech Co., Ltd.; WO2004/35533; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 85006-25-3

General procedure: Method D: To a solution of acyl Meldrum?s acid (1.69mmol, 1.8equiv) in dry toluene (4.5mL) at room temperature was added N,O-bis(tert-butoxycarbonyl)hydroxylamine (219mg, 0.938mmol, 1.0equiv), and the reaction mixture was immersed in an oil bath preheated to 90C. The reaction was monitored for the complete consumption of N,O-bis(tert-butoxycarbonyl)hydroxylamine. Leaving the reaction for longer time can lead to loss in yield and competing side reactions. After concentration in vacuo, the residue was purified on silica gel chromatography using 5% ethyl acetate in hexane to yield beta-keto hydroxamic acid (12a, d, f-i, l, p) as colorless oil.

According to the analysis of related databases, 85006-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Verma, Astha; Wong, Dawn M.; Islam, Rafique; Tong, Fan; Ghavami, Maryam; Mutunga, James M.; Slebodnick, Carla; Li, Jianyong; Viayna, Elisabet; Lam, Polo C.-H.; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1321 – 1340;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 85006-25-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Method D: To a solution of acyl Meldrum?s acid (1.69mmol, 1.8equiv) in dry toluene (4.5mL) at room temperature was added N,O-bis(tert-butoxycarbonyl)hydroxylamine (219mg, 0.938mmol, 1.0equiv), and the reaction mixture was immersed in an oil bath preheated to 90C. The reaction was monitored for the complete consumption of N,O-bis(tert-butoxycarbonyl)hydroxylamine. Leaving the reaction for longer time can lead to loss in yield and competing side reactions. After concentration in vacuo, the residue was purified on silica gel chromatography using 5% ethyl acetate in hexane to yield beta-keto hydroxamic acid (12a, d, f-i, l, p) as colorless oil.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Verma, Astha; Wong, Dawn M.; Islam, Rafique; Tong, Fan; Ghavami, Maryam; Mutunga, James M.; Slebodnick, Carla; Li, Jianyong; Viayna, Elisabet; Lam, Polo C.-H.; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1321 – 1340;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 85006-25-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 85006-25-3 name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation 2 [tert-Butoxycarbonyl-[(4-methoxyphenyl)methyl]amino] tert-butyl carbonate A 20 L reactor, under nitrogen is charged with (tert-butoxycarbonylamino) tert- butyl carbonate (812.9 g, 3.48 mol), dimethylformamide (4.4 L), potassium carbonate (626.5 g, 4.52 mol) and l -(chloromethyl)-4-methoxy -benzene (462 mL, 2.56 mol). The mixture is stirred at 40 C overnight. lH NMR analysis shows incomplete reaction. Additional potassium carbonate (626.5 g, 4.52 mol) is added and the mixture is stirred at 40 C. lH NMR analysis after 48 hours shows the reaction is still incomplete. Additional potassium carbonate (482 g, 3.49 mol) is added and the mixture is stirred at 40 C. lH NMR analysis after overnight reaction shows complete reaction with no starting materials remaining. Water (5 L) and MTBE (5 L) are added and the layers are separated. The organic layer is washed with water (3×3 L), dried over sodium sulphate, and concentrated to give the title compound (1.21 Kg, 98%). 1H NMR (d6-DMSO) delta 7.20 (d, J= 8.3 Hz, 2H), 6.91 (d, J= 8.3 Hz, 2H), 3.73 (s, 2H), 3.35 (s, 3H), 1.41 (s, 18H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (tert-butoxycarbonyl)oxycarbamate, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; MARTIN, Fionna Mitchell; WO2015/138208; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (tert-butoxycarbonyl)oxycarbamate

Example 17: 7¾ -butyl i2-fl2-amino-3-chloro-6,7,10,ll-tetrahydro-7,ll- methano cvcloocta[bl uinolin-9-yl)ethyll (tert- butox carbonvDoxyl carbamate (HUP 16)A solution of tert-butyl-N-(tert-butoxycarbonyl)-carbamate (140 mg, 0.6 mmol) in anhydrous DMF (1.3 mL) was treated with sodium hydride (60% in oil, 26 mg, 0.65 mmol). The reaction mixture was stirred 40 min at r.t. and treated with a solution of mesylate (HUP 13) (157 mg, 0.4 mmol) in anhydrous DMF (2 mL). The reaction mixture was stirred at r.t. for 120 h, then at 60 C for 5 h. The mixture was then diluted with water (50 mL) and extracted with AcOEt (3 x 30 mL). The combined organic layers were washed with brine (50 mL), then water (50 mL), dried with Na2S04 and concentrated under reduced pressure to afford a yellow solid (313 mg). Purification by flash chromatography (AcOEt / MeOH 10/0 to 8/2, v/v) afforded the desired Huprine (HUP 16) as a white solid (98 mg, 46%).Rf (AcOEt / MeOH 8/2, v/v) = 0.50.m.p. = 114C (decomposition).1H NMR (300 MHz, CDC13): delta = 1.41 (s, 9H, N-Boc or O-Boc), 1.46 (s, 9H, N- Boc or O-Boc), 1.84-2.02 (m, 3H, Hio, ¾), 2.10-2.22 (m, 2H, Hi4), 2.52 (dd, J = 17.1 Hz, J = 3.4 Hz, 1H, ¾), 2.67-2.71 (m, 1H, H7), 2.89 (d, J = 17.5 Hz, 1H, H6), 3.06 (dd, J = 17.6 Hz, J = 5.6 Hz, 1H, H6), 3.14-3.18 (m, 1H, Hn), 3.66-3.88 (m, 2H, His), 5.03 (brs, 2H, NH2), 5.56 (d, J = 5.1 Hz, 1H, H8), 7.21 (dd, J = 9.0 Hz, J= 1.9 Hz, 1H, H2), 7.67 (d, J= 9.0 Hz, 1H, ¾), 7.77 (d, J= 1.9 Hz, 1H, H4). 13C NMR (75 MHz, CDC13): delta = 27.4 (Cn), 27.6 (N-Boc or O-Boc), 28.1 (N-Boc or O-Boc), 28.2 (C7), 28.9 (C10), 33.8 (C13), 34.8 (Ci4), 39.4 (C6), 68.1 (Ci5), 82.3 (C-Me3 of N-Boc), 84.9 (C-Me3 of O-Boc), 115.1 (Cna or Ci2a), 115.8 (Cna or Ciza), 122.0 (Ci), 124.6 (C2), 126.9 (C4), 127.0 (C8), 132.9 (C3), 134.6 (C9), 146.5 (C4a or Ci2), 147.0 (C4a or C12), 152.2 (C=0 of N-Boc), 154.8 (C=0 of O-Boc), 158.3 (C5a).MS (ESI+): m/z (%): 530.20 (100) [M+H]+, 532.20 (39).ICso rh-AC E : 14.8 +/- 3.2 nM.ICso r/i-BuChE : 421 +/- 72 nM.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; UNIVERSITE DE ROUEN; RONCO, Cyril; RENARD, Pierre Yves; JEAN, Ludovic; NACHON, Florian; ROMIEU, Anthony; WO2011/124712; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 85006-25-3,Some common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Tert-butyl (tert-butoxycarbonyl)oxycarbamate (70 mg) and 1- (bromomethyl) -2-fluorobenzene (56.7 mg) were dissolved in CH 2Cl 2(7 ml) . The mixture was added 1M NaOH (0.33 ml) and tetrabutylammonium bromide(4.83 mg) , and stirred at room temperature for overnight. The resulting mixture was washed with water and dried with Na 2SO 4, concentrated in vacuo and purification by silica gel chromatography to give tert-butyl ( (tert-butoxycarbonyl) oxy) (2-fluorobenzyl) carbamate (82 mg, 80%) . 1HNMR (400 MHz, CDCl 3): delta 7.31-7.37 (m, 4H) , 4.52(s, 2H) , 1.46 (s, 9H) , 1.44 (s, 9H) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (tert-butoxycarbonyl)oxycarbamate, its application will become more common.

Reference:
Patent; SU, Yaning; SIRONAX LTD; ZHANG, Zhiyuan; YANG, Yi; WANG, Guozheng; LIU, Wendong; MA, Yongfen; REN, Yan; (74 pag.)WO2020/103859; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 85006-25-3, A common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics