benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate

Base Information

• Chemical Name: benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate
• CAS No.: 78184-08-4
• Molecular Formula: C12H14N2O4
• Molecular Weight: 250.254
• DSSTox Substance ID: DTXSID10511056
• Mol file: 78184-08-4.mol

Synonyms:78184-08-4;benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate;benzyl 3-methoxy-2-oxo-3-azetidinylcarbamate;SCHEMBL10546923;DTXSID10511056;UMGXLKSMZPNOAQ-UHFFFAOYSA-N;3-Methoxy-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone;AKOS015907086;Benzyl (3-methoxy-2-oxoazetidin-3-yl)carbamate

Chemical Property of benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 250.09535693
• Heavy Atom Count: 18
• Complexity: 328

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1(CNC1=O)NC(=O)OCC2=CC=CC=C2

Technology Process of benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate

There total 6 articles about benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate 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:

1-chloro-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-2-azetidinone + acetic acid phenethyl ester (103-45-7) → 3-methoxy-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone (78184-08-4)

Guidance literature:

With lithium methanolate; acetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol;

Reference yield:

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate (80082-81-1) → 3-methoxy-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone (78184-08-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / tert-butyl-hypochlorite, sodium borate / methanol / 0.5 h / 0 °C

3: trimethyl phosphite

With sodium borate; tert-butylhypochlorite; phosphorous acid trimethyl ester; In methanol;

DOI:10.1021/jo00340a049

Reference yield:

methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate (78115-03-4) → 3-methoxy-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone (78184-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 84.9 percent / tetrahydrofuran / 1 h / -10 °C

2: 1.) O₃ / 2.) methanol

With ozone; In tetrahydrofuran;

DOI:10.1248/cpb.31.2200

upstream raw materials:

sodium methylate

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

(1-Chloro-3-methoxy-2-oxo-azetidin-3-yl)-carbamic acid benzyl ester

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

Downstream raw materials:

(3R)-3--3-methoxy-2-azetidinone

(3S)-3--3-methoxy-2-azetidinone

3-benzyloxycarbonylamino-3-methoxy-2-oxo-1-azetidinesulfonic acid, potassium salt