2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid

Base Information

• Chemical Name: 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid
• CAS No.: 122692-62-0
• Molecular Formula: C₁₅H₁₅N₃O₆S
• Molecular Weight: 365.367
• Mol file: 122692-62-0.mol

Synonyms:2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid

Chemical Property of 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid

There total 4 articles about 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid 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: 67.0%

2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>-trichloroethyl acetate (122692-61-9) → 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid (122692-62-0)

Guidance literature:

With acetic acid; zinc; In N,N-dimethyl-formamide; at 0 ℃; for 4h;

DOI:10.1016/0223-5234(88)90100-6

Reference yield:

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-acetic acid-β-trichloroethyl ester (87996-82-5) → 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid (122692-62-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / 1.2 N aq HCl / dimethylformamide / 1 h / Ambient temperature

2: 82 percent / triethylamine / dimethylformamide / 1 h / 0 °C / then 20 deg C

3: 79 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C / then 20 deg C

4: 67 percent / zinc dust, acetic acid / dimethylformamide / 4 h / 0 °C

With hydrogenchloride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(88)90100-6

Reference yield:

2-<3-phenylacetamido-4-thiol-(3R,4R)-azetidin-2-on-1-yl>-trichloroethyl acetate (122691-74-1) → 2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>acetic acid (122692-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / triethylamine / dimethylformamide / 1 h / 0 °C / then 20 deg C

2: 79 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C / then 20 deg C

3: 67 percent / zinc dust, acetic acid / dimethylformamide / 4 h / 0 °C

With acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(88)90100-6

upstream raw materials:

2-<3-phenylacetamido-4-cyanomethylsulfonyl-(3R,4R)-azetidin-2-on-1-yl>-trichloroethyl acetate

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-acetic acid-β-trichloroethyl ester

2-<3-phenylacetamido-4-thiol-(3R,4R)-azetidin-2-on-1-yl>-trichloroethyl acetate

2-<3-phenylacetamido-4-thiocyanomethyl-(3R,4R)-azetidin-2-on-1-yl>-trichloroethyl acetate