(S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

Base Information

Chemical Name:(S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester
CAS No.:613688-75-8
Molecular Formula:C₂₂H₂₆N₂O₃
Molecular Weight:366.46
Hs Code.:

Synonyms:(S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

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Chemical Property of (S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

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Technology Process of (S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

There total 4 articles about (S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

: 2491-20-5
L-alanine methyl ester hydrochloride

: (2R,3S,4S)-1-benzyl-4-methyl-3-phenylazetidine-2-carboxylic acid hydrochloride

: 613688-75-8
(S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

Guidance literature:: With 2-hydroxybenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/S0957-4166(03)00493-2

Reference yield:

: 61347-76-0
NH-benzyl-(1R,2S)-norephedrine

: 613688-75-8
(S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / K₂CO₃ / acetonitrile / 12 h / Heating

2.1: 77 percent / thionyl chloride / CH₂Cl₂ / 1 h / Heating

3.1: LiHMDS / tetrahydrofuran / 1 h / -78 - -50 °C

3.2: aq. HCl / acetic acid / 72 h / 100 °C

4.1: 72 percent / 2-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide; Et₃N / CH₂Cl₂ / 12 h / 20 °C

With 2-hydroxybenzotriazole; thionyl chloride; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/S0957-4166(03)00493-2

Reference yield:

: 613688-63-4
[benzyl[(1S,2R)-2-chloro-1-methyl-2-phenylethyl]amino]acetonitrile

: 613688-75-8
(S)-2-[((2R,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 - -50 °C

1.2: aq. HCl / acetic acid / 72 h / 100 °C

2.1: 72 percent / 2-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide; Et₃N / CH₂Cl₂ / 12 h / 20 °C

With 2-hydroxybenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0957-4166(03)00493-2