((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 202919-23-1
• Molecular Formula: C₁₅H₁₃Cl₃N₂O₄S
• Molecular Weight: 423.704
• Mol file: 202919-23-1.mol

Synonyms:

Chemical Property of ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester

There total 2 articles about ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl 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: 44.0%

1,1,1-trichloroethanol (115-20-8) + ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid (202918-99-8) → ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester (202919-23-1)

Guidance literature:

With N,N-diethyl-2-propynylamine; In dichloromethane; for 3h; -60 deg C -> room temperature;

Reference yield:

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one (35500-75-5) → ((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester (202919-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Triton B / methanol; dimethylformamide / 1.) -30 deg C, 15 min, 2.) 0 deg C, 1 h, 3.) 20 deg C, 2 h

2: 44 percent / N,N-(diethyl)amino-1-propyne / CH₂Cl₂ / 3 h / -60 deg C -> room temperature

With N,N-diethyl-2-propynylamine; N-benzyl-trimethylammonium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid 2,2,2-trichloro-ethyl ester (202919-23-1) → [(2R,3R)-2-Mercapto-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 2,2,2-trichloro-ethyl ester (202919-01-5)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; Yield given; 1.) 0 deg C, 10 min, 2.) 20 deg C, 1 h;

upstream raw materials:

1,1,1-trichloroethanol

((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-acetic acid

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one

Downstream raw materials:

[(2R,3R)-2-Mercapto-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 2,2,2-trichloro-ethyl ester

[(2R,3R)-2-Benzylsulfanyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 2,2,2-trichloro-ethyl ester

[(3R,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-phenylmethanesulfonyl-azetidin-1-yl]-acetic acid 2,2,2-trichloro-ethyl ester