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

Base Information

• Chemical Name: methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate
• CAS No.: 78115-03-4
• Molecular Formula: C₁₇H₂₀N₂O₅
• Molecular Weight: 332.356
• Mol file: 78115-03-4.mol

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

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

There total 14 articles about methyl 2-<(3S)-3-benzyloxycarbonylamino-2-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: 84.9%

benzyl chloroformate (501-53-1,94274-21-2) + (3S)-3-amino-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-2-azetidinone (78129-77-8) → methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate (78115-03-4)

Guidance literature:

With methyloxirane; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.31.1874

Reference yield:

2-{(2R,3R)-2-[(2R,3R)-1-(1-Methoxycarbonyl-2-methyl-propenyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester (62284-27-9) → methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate (78115-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76.2 percent / Raney nickel / ethanol / 0.5 h / 50 °C

2: 1.) PCl₅ / 1.) pyridine, CH₂Cl₂, 0 degC, 70 min; 2.) n-butyl alcohol, 0 degC, 1 h

3: 84.9 percent / propylene oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

With phosphorus pentachloride; methyloxirane; nickel; In ethanol; dichloromethane;

DOI:10.1248/cpb.31.1874

Reference yield:

2-[(2R)-2r-benzothiazol-2-yldisulfanyl-4-oxo-3c-(2-phenyl-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester (61603-43-8) → methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate (78115-03-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Raney nickel / ethanol / Ambient temperature

2: 43.9 percent / benzene / 0.75 h / 100 °C

3: 24.8 percent / Raney nickel / tetrahydrofuran / 6 h / Heating

4: 1.) PCl₅ / 1.) pyridine, CH₂Cl₂, 0 degC, 70 min; 2.) n-butyl alcohol, 0 degC, 1 h

5: 84.9 percent / propylene oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

With phosphorus pentachloride; methyloxirane; nickel; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1248/cpb.31.1874

upstream raw materials:

benzyl chloroformate

(3S)-3-amino-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-2-azetidinone

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

6-Aminopenicillanic Acid

Downstream raw materials:

3-methoxy-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone

(3S)-(benzyloxycarbonyl)amino-2-oxo-azetidine-1-sulfonic acid, pyridinium salt

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

2-(3-Benzyloxycarbonylamino-3-methoxy-2-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester