Category: 87905-98-4

Electric Literature of 87905-98-4, A common heterocyclic compound, 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, molecular formula is C13H19NO3, 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.

<5-4> Preparation of 1-O-(N-Carbobenzoxy-6-Aminopentyl)-2,3,4,6-tetra-O-Benzoyl-D-Glucopyranoside N-carbobenzoxy-6-aminopentanol (0.32 g, 1.35 mmol) and trimethylsilyl trifluoromethanesulfonate (0.25 ml, 1.35 mmol) were dissolved in dichloromethane (10 ml) and cooled to 0 C. To this solution, was added a solution obtained by dissolving the compound obtained in Preparative Example <5-3> (1 g, 1.4 mmol) in dichloromethane (25 ml), and the mixture thus obtained was stirred for 2 hours.After the completion of the reaction, the reaction mixture was filtered through celite. The filtrate thus obtained was washed with saturated aqueous NaHCO3 and aqueous NaCl. The product thus obtained was dried over Na2SO4, concentrated under a reduced pressure, and then purified by column chromatography (ethyl acetate_hexane=1:2) to obtain the title compound as a transparent sticky oil (0.8 g).1H NMR (CDCl3): delta 1.20-1.54 (m, 6H), 2.93-2.95 (d, J=6.1 Hz, 2H), 3.51-3.54 (m, 1H), 3.88-3.95 (m, 1H), 4.10-4.17 (m, 1H, H-5), 4.47 (dd, J=12.2 Hz, 5.0 Hz, 1H, H-6b), 4.63 (d, J=11.9 Hz, 2H, H-6b, NH), 4.81 (d, J=7.7 Hz, 1H, H-1), 5.08 (s, 1H, benzyl), 5.52 (t, J=9.4 Hz, 1H, H-2), 5.68 (t, J=9.7 Hz, 1H, H-4), 5.91 (t, J=9.6 Hz, 1H, H-3), 7.26-8.03 (m, 25H, arom).

The synthetic route of 87905-98-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chung, Sung-Kee; Lee, Woo Sirl; Kim, Boram; Im, Jungkyun; Ghosh, Subhash C.; US2011/224423; (2011); 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. 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Benzoyl chloride (0.88 mL, 7.59 mmol) was added dropwise to a stirred solution of benzyl (5-hydroxypentyl) carbamate (commercially available) (1.5 g, 6.32 mmol) in anhydrous CH2C12 (15 mL) containing Et3N (1.76 mL, 1.26 mmol) at 0 C. After 1 minute DMAP (1.7 g, 13.9 mmol) in anhydrous CH2CI2 (10 mL) was added dropwise to the reaction mixture and stirred at rt overnight. The resulting mixture was diluted with CH2CI2 (-30 mL) and washed with aq. HC1 (1M, 1 x 10 mL), water (60 mL), sat. aq. NaHC03 (30 mL), and brine (30 mL). The organic phase was separated, dried over MgS04, and concentrated in vacuo. The residue was quickly filtered off on silica gel (ethyl acetate – hexane gradient elution) to afford the almost pure compound as oil. This crude material was directly used for benzylation. To the solution of benzoyl protected compound (0.9 g, 2.63 mmol) dissolved in anhydrous DMF (10 mL) was added NaH (0.12 g, 2.89 mmol) at 0 C. The mixture was stirred at 0 C for 45 min, and then BnBr (0.37 mL, 3.16 mmol) were added. After stirring for another 12 h when TLC showed that the reaction was completed, it was quenched with H20 at 0 C, and the mixture was diluted with EtOAc. The aqueous layer was extracted with EtOAc (5 chi 25 mL), and the organic phases were combined and dried over Na2S04. The desired product S13 (1.093 g, 96.1%) was obtained upon flash column chromatography (ethyl acetate – hexane gradient elution) of the condensed product.

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; THE SECRETARY OF STATE FOR ENVIRONMENT, FOOD AND RURAL AFFAIRS; THE GOVERNORS OF THE UNIVERSITY OF ALBERTA; MCGIVEN, John; HOWELLS, Laurence; DUNCOMBE, Lucy; BUNDLE, David; MANDAL, Satadru Sekhar; SARKAR, Susmita; (101 pag.)WO2018/83490; (2018); A2;,
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. 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, A new synthetic method of this compound is introduced below., Product Details of 87905-98-4

Benzoyl chloride (0.88 mL, 7.59 mmol) was added dropwise to a stirred solution of benzyl (5-hydroxypentyl) carbamate (commercially available) (1.5 g, 6.32 mmol) in anhydrous CH2C12 (15 mL) containing Et3N (1.76 mL, 1.26 mmol) at 0 C. After 1 minute DMAP (1.7 g, 13.9 mmol) in anhydrous CH2CI2 (10 mL) was added dropwise to the reaction mixture and stirred at rt overnight. The resulting mixture was diluted with CH2CI2 (-30 mL) and washed with aq. HC1 (1M, 1 x 10 mL), water (60 mL), sat. aq. NaHC03 (30 mL), and brine (30 mL). The organic phase was separated, dried over MgS04, and concentrated in vacuo. The residue was quickly filtered off on silica gel (ethyl acetate – hexane gradient elution) to afford the almost pure compound as oil. This crude material was directly used for benzylation. To the solution of benzoyl protected compound (0.9 g, 2.63 mmol) dissolved in anhydrous DMF (10 mL) was added NaH (0.12 g, 2.89 mmol) at 0 C. The mixture was stirred at 0 C for 45 min, and then BnBr (0.37 mL, 3.16 mmol) were added. After stirring for another 12 h when TLC showed that the reaction was completed, it was quenched with H20 at 0 C, and the mixture was diluted with EtOAc. The aqueous layer was extracted with EtOAc (5 chi 25 mL), and the organic phases were combined and dried over Na2S04. The desired product S13 (1.093 g, 96.1%) was obtained upon flash column chromatography (ethyl acetate – hexane gradient elution) of the condensed product.

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; THE SECRETARY OF STATE FOR ENVIRONMENT, FOOD AND RURAL AFFAIRS; THE GOVERNORS OF THE UNIVERSITY OF ALBERTA; MCGIVEN, John; HOWELLS, Laurence; DUNCOMBE, Lucy; BUNDLE, David; MANDAL, Satadru Sekhar; SARKAR, Susmita; (101 pag.)WO2018/83490; (2018); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, 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 87905-98-4, category: amides-buliding-blocks

To a solution of oxalyl chloride (814 mul, 9.62 mmol, 2.3 equiv.) in dried dichloromethane (25 ml) under an inert atmosphere was slowly added a solution of dimethylsulfoxyde (1.3 ml, 18.2 mmol, 4.3 equiv.) in dried dichloromethane (10 ml). The solution was stirred for 5 min at -70C then a suspension of benzyl ((5-hydroxypentyl)carbamate) [21] (1 g, 4.22 mmol, 1 equiv.) in dried dichloromethane (25 ml) was transferred via canula. The mixture was stirred for 25 min at -70C then triethylamine (11.7 ml, 8.44 mmol, 20 equiv.) was slowly added. The reaction mixture was stirred for 20 min at -70C and 15 min at room temperature and then quenched by addition to 600 ml of water. The aqueous phase was extracted with diethylether (3×100 ml) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the aldehyde (1.1 g) used in the next step without purification. To a suspension of potassium cyanide (249 mg, 3.83 mmol, 1 equiv.) in water (520 mul) were added ammonium chloride (203 mg, 3.83 mmol, 1 equiv.) and ammonium hydroxide 33% (1.32 ml; 20.3 mmol, 5.3 equiv.). The reaction mixture was stirred for 15 min at 0C then a solution of the aldehyde (900 mg, 3.83 mmol, 1 equiv.) in dioxane (1.35 ml) was added dropwise over 20 min. The mixture was stirred for 20 h and then quenched by addition of water (10 ml) and diethyl ether (30 ml). The aqueous phase was acidified with HCl 1 M (50 ml), washed with diethyl ether (3×20 ml), basified to pH = 12 with NaOH 1 M (20 ml) and then extracted with dichloromethane (4×10 ml). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the protected aminonitrile; yield: 905 mg (91%). 1H NMR (MeOD-d4, 300 MHz) delta 1.52 (m, 4H, H4, H5), 1.71 (m, 2H, H3), 3.14 (t, 2H, H6), 3.71 (t, 2H,H2), 5.06 (s, 2H, H8), 7.34 (m, 5H, H10-H12); 13C NMR (MeOD-d4, 75 MHz) . 23.9 (C4), 30.4 (C5), 35.9 (C3), 41.5 (C6), 44.2 (C2), 67.4(C8), 123.1 (C1), 128.8-129.6 (C10-C12), 138.6 (C9), 159.0 (C7) (seeSI, Figs. S3 and S4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl (5-hydroxypentyl)carbamate, and friends who are interested can also refer to it.

Reference:
Article; Bordier, Franck; Stam, Mark; Darii, Ekaterina; Tricot, Sabine; Fossey, Aurelie; Rohault, Johanna; Debard, Adrien; Mariage, Aline; Pellouin, Virginie; Petit, Jean-Louis; Perret, Alain; Vallenet, David; Salanoubat, Marcel; Weissenbach, Jean; Vergne-Vaxelaire, Carine; De Berardinis, Veronique; Zaparucha, Anne; Journal of Molecular Catalysis B: Enzymatic; vol. 107; (2014); p. 79 – 88;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 87905-98-4, A common heterocyclic compound, 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, molecular formula is C13H19NO3, 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.

<5-4> Preparation of 1-O-(N-Carbobenzoxy-6-Aminopentyl)-2,3,4,6-tetra-O-Benzoyl-D-Glucopyranoside N-carbobenzoxy-6-aminopentanol (0.32 g, 1.35 mmol) and trimethylsilyl trifluoromethanesulfonate (0.25 ml, 1.35 mmol) were dissolved in dichloromethane (10 ml) and cooled to 0 C. To this solution, was added a solution obtained by dissolving the compound obtained in Preparative Example <5-3> (1 g, 1.4 mmol) in dichloromethane (25 ml), and the mixture thus obtained was stirred for 2 hours.After the completion of the reaction, the reaction mixture was filtered through celite. The filtrate thus obtained was washed with saturated aqueous NaHCO3 and aqueous NaCl. The product thus obtained was dried over Na2SO4, concentrated under a reduced pressure, and then purified by column chromatography (ethyl acetate_hexane=1:2) to obtain the title compound as a transparent sticky oil (0.8 g).1H NMR (CDCl3): delta 1.20-1.54 (m, 6H), 2.93-2.95 (d, J=6.1 Hz, 2H), 3.51-3.54 (m, 1H), 3.88-3.95 (m, 1H), 4.10-4.17 (m, 1H, H-5), 4.47 (dd, J=12.2 Hz, 5.0 Hz, 1H, H-6b), 4.63 (d, J=11.9 Hz, 2H, H-6b, NH), 4.81 (d, J=7.7 Hz, 1H, H-1), 5.08 (s, 1H, benzyl), 5.52 (t, J=9.4 Hz, 1H, H-2), 5.68 (t, J=9.7 Hz, 1H, H-4), 5.91 (t, J=9.6 Hz, 1H, H-3), 7.26-8.03 (m, 25H, arom).

The synthetic route of 87905-98-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chung, Sung-Kee; Lee, Woo Sirl; Kim, Boram; Im, Jungkyun; Ghosh, Subhash C.; US2011/224423; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics