methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate

Base Information

• Chemical Name: methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate
• CAS No.: 56614-35-8
• Molecular Formula: C₁₇H₁₉ClN₂O₅
• Molecular Weight: 366.801
• Mol file: 56614-35-8.mol

Synonyms:methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate

Chemical Property of methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate

There total 4 articles about methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate 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: 69.0%

methyl (3S,5R,6R)-6-benzyloxycarbonylamino-2,2-dimethylpenam-3-carboxylate (81651-37-8) → methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate (56614-35-8)

Guidance literature:

With chlorine; In tetrachloromethane; dichloromethane; 1.) -70 deg C, 1 h, 2.) 20 deg C, 30 min;

Reference yield:

<2S-<2α,5α,6β>>-3,3-dimethyl-7-oxo-6-<<(phenylmethoxy)carbonyl>amino>-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid (23536-59-6) → methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate (56614-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / dimethylformamide / 2 h

2: 69 percent / Cl₂ / CCl₄; CH₂Cl₂ / 1.) -70 deg C, 1 h, 2.) 20 deg C, 30 min

With chlorine; potassium carbonate; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl 2-<(2S,3R)-3-benzyloxycarbonylamino-2-chloro-4-oxoazetidin-1-yl>-3-methylbut-2-enoate (56614-35-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / NaHCO₃ / diethyl ether; H₂O / 2 h

2: K₂CO₃ / dimethylformamide / 2 h

3: 69 percent / Cl₂ / CCl₄; CH₂Cl₂ / 1.) -70 deg C, 1 h, 2.) 20 deg C, 30 min

With chlorine; sodium hydrogencarbonate; potassium carbonate; In tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

methyl (3S,5R,6R)-6-benzyloxycarbonylamino-2,2-dimethylpenam-3-carboxylate

<2S-<2α,5α,6β>>-3,3-dimethyl-7-oxo-6-<<(phenylmethoxy)carbonyl>amino>-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid

benzyl chloroformate

Downstream raw materials:

methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate