(S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester
• CAS No.: 389806-09-1
• Molecular Formula: C₁₉H₁₉N₃O₇S
• Molecular Weight: 433.442
• Mol file: 389806-09-1.mol

Synonyms:(S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester

Chemical Property of (S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester

There total 2 articles about (S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl 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: 73.0%

H-Ala-OBzl (17831-01-5) + (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester (389806-02-4) → (S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester (389806-09-1)

Guidance literature:

H-Ala-OBzl; (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester; With triethylamine; In tetrahydrofuran; at 20 ℃; for 16h;

With trifluoroacetic acid; at 20 ℃; for 0.5h;

With hydrogenchloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1055/s-2001-18090

Reference yield:

N-(2-nitrobenzenesulfonyl)-L-serine tert-butyl ester (389806-01-3) → (S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester (389806-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / Ph₃P; DEAD / tetrahydrofuran / 1 h / -5 °C

2.1: Et₃N / tetrahydrofuran / 16 h / 20 °C

2.2: TFA / 0.5 h / 20 °C

2.3: 73 percent / aq. HCl; EDC; DIPEA / CH₂Cl₂ / 16 h / 20 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1.1: Mitsunobu reaction;

DOI:10.1055/s-2001-18090

Reference yield:

(S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester (389806-09-1) → (S)-2-((S)-3-Benzyloxycarbonylamino-2-oxo-azetidin-1-yl)-propionic acid benzyl ester (389806-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / CH₂Cl₂ / 6 h / 0 °C

2: 99 percent / PhSH; DIPEA / dimethylformamide / 4 h / 20 °C

With pyridine; thiophenol; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-18090

upstream raw materials:

H-Ala-OBzl

(S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester

N-(2-nitrobenzenesulfonyl)-L-serine tert-butyl ester

Downstream raw materials:

(S)-2-((S)-3-amino-2-oxo-azetidin-1-yl)-propionic acid

(S)-2-((S)-3-Benzyloxycarbonylamino-2-oxo-azetidin-1-yl)-propionic acid benzyl ester