[(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl ester

Base Information

• Chemical Name: [(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl ester
• CAS No.: 66260-72-8
• Molecular Formula: C₁₆H₁₈N₂O₇S
• Molecular Weight: 382.394

Synonyms:[(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl ester

Chemical Property of [(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl ester

There total 3 articles about [(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl 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: 81.0%

N-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide (73395-53-6) + malonic acid dimethyl ester (108-59-8) → [4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-malonic acid dimethyl ester (66260-72-8,71698-45-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.75h;

DOI:10.1016/S0040-4039(01)91387-5

Reference yield:

2-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester (75283-03-3) → [4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-malonic acid dimethyl ester (66260-72-8,71698-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1., ozonolysis; 2., treatment with methanol

2: 81 percent / NaH / tetrahydrofuran / 0.75 h / 0 °C

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)91387-5

Reference yield:

→ [(2R)-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-2r-ylsulfanyl]-malonic acid dimethyl ester (66260-72-8)

Guidance literature:

Thiazolin 31, 2,6-Di-tert.-butyl-4-methylphenol, Brommalonsaeuredimethylester;

upstream raw materials:

N-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

malonic acid dimethyl ester

2-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester

Downstream raw materials:

(5R)-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2ξ,3,3-tricarboxylic acid 2-tert-butyl ester 3,3-dimethyl ester

2-[1-[Hydroxy-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-malonic acid dimethyl ester

7-Oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3,3-tricarboxylic acid dimethyl ester

2-[1-[Chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-malonic acid dimethyl ester

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