Category: 94838-59-2

Application of 94838-59-2, A common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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.

To a solution of tert-butyl 2-(4-aminophenyl)ethylcarbamate (200 mg, 0.85 mmol) in Toluene (2 mL) was added N,N-dimethylformamide azine (120 mg, 0.85 mmol, prepared by the method described in Bioorg. Med. Chem. Letters, 6(15): 1825-1830, 1996) and TsOH.H2O (16 mg, 0.08 mmol). Resulting solution was heated to reflux and stirred overnight. Reaction mixture was cooled, concentrated in vacuo, and subjected to silica gel chromatography eluting with 2%-5% MeOH in CH2Cl2 to give 250 mg (100%) tert-butyl 2-[4-(4H-1,2,4-triazol-4-yl)phenyl]ethyl-carbamate. LCMS (ES) 289.3 m/z (M+H)+.

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; Su, Dai-Shi; Bock, Mark G.; US2005/20591; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 94838-59-2, 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. 94838-59-2 name is tert-Butyl 4-aminophenethylcarbamate, 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.

A solution of formaldehyde (0.303 g, 4 mmol, 40% in water), fert-butyl 4- aminophenethylcarbamate (1.135 g, 4.8 mmol) and NaBH3CN (1.257 g, 20 mmol) in methanol (14 mL) was stirred at room temperature for 4 h. Water (30 mL) was added to the reaction mixture afterward and the mixture was extracted with ethyl acetate (30 mL 3). The organic layer was washed with water (20 mL) and brine (20 mL), dried with NaiSCri and concentrated. The residue was purified by column chromatography to afford the title compound as colorless oil (0.337 g, 33.7 % yield). NMR (500 MHz, DMSO-riri) d: (d, J= 8.3 Hz, 2H), 6.79 (t, J= 5.3 Hz, 1H), 6.46 (d, J= 8.4 Hz, 2H), 5.41 (q, J= 5.0 Hz, 1H), 3.03 (dd, J= 14.9, 6.1 Hz, 2H), 2.64 (d, J= 5.2 Hz, 3H), 2.54 – 2.51 (m, 2H), 1.38 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-aminophenethylcarbamate, and friends who are interested can also refer to it.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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 94838-59-2. 94838-59-2

A mixture of 2-Deoxy-D-ribose (Apollo, 2g, 14.8 mmol), tert-butyl 4- aminophenetylcarbamate (Ark Pharm, 5.14 g, 20.7 mmol) and montmorillonite (12 g) was stirred at RT in MeCN (100 mL) for three days. The reaction mixture was then filtered through a celite pad which was subsequently washed with EtOAc. The filtrate was concentrated under reduced pressure. Purification of this crude (5.2 g) by flash chromatography on silica (Cyclohexane: EtOAc, gradient from 7:3 to 6:4) afforded the title compounds: First eluting fraction (Intermediate 1): [2-((lS,9S,10S)-10-Hydroxy-12-oxa-8-aza- tricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-ethyl]-carbamic acid tert-butyl ester (1.88 g, 37%), yellow solid, Rf=0.35 (Cyclohexane:EtOAc, 2:8), lH NMR (CDC13) : 6.98 (dd, IH, J=8.1 Hz, J=1.5 Hz), 6.94 (dd, IH, J=1.5 Hz), 6.59 (d, IH, J=8.1 Hz), 4.67-4.36 (m, IH), 4.60-4.50 (m, IH), 4.45-4.35 (m, IH), 3.81-3.65 (m, 2H), 3.63 (brs, IH), 3.37-3.20 (m, 2H), 2.91 (t, IH, J=10.0 Hz), 2.71-2.61 (m, 2H), 2.15-2.05 (m, 2H), 2.15-2.05 (m, 2H), 1.88 (dd, IH, J=4.7 Hz, J=2.0 Hz), 1.43 (s, 9H). Second eluting fraction (intyermediate 2): [2-((lR,9R,10S)-10-Hydroxy-12-oxa-8-aza- tricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-ethyl]-carbamic acid tert-butyl ester (2.0 g, 41%), white solid, Rf=0.25 (Cyclohexane:EtOAc, 2:8), lH NMR (CDCI3) : 7.01-6.93 (m, 2H), 6.51 (d, IH, J=8.0 Hz), 4.71-4.68 (m, IH), 4.60-4.48 (m,lH), 3.67-3.61 (m, IH), 3.59-3.48 (m, 3H), 3.38- 3.24 (m, 2H), 2.67 (t, 2H, J=7.0 Hz), 2.56 (dt, IH, J=13.5 Hz, J=3.0 Hz, J=3.0 Hz), 2.31 (d, IH, 7.3 Hz), 1.59-1.53 (m,lH), 1.43 (s, 9H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of tert-Butyl 4-aminophenethylcarbamate.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; JOHNSON, Theresa L.; GRAEDLER, Ulrich; JIANG, Xuliang; ROCHE, Didier; LEMOINE, Hugues; GILARDONE, Marine; (61 pag.)WO2017/173049; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics