(2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester
CAS No.:84187-64-4
Molecular Formula:C₁₉H₁₈ClN₅O₆S
Molecular Weight:479.901
Hs Code.:

Synonyms:(2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

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Technology Process of (2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

There total 5 articles about (2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl 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: 96.0%

: 72079-37-9,84187-48-4,104159-67-3
cis-3-amino-4-methoxycarbonyl-2-azetidinone

: 92973-48-3
[(Z)-Benzyloxyimino]-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetyl chloride; hydrochloride

: 84187-64-4
(2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

Guidance literature:: With sodium hydrogencarbonate; In tetrahydrofuran; water; for 2h; Ambient temperature;
DOI:10.1248/cpb.32.2646

Reference yield:

: 61964-78-1,84187-43-9,88792-16-9,88792-17-0,88852-05-5,97591-35-0
cis-3-amino-1-(2,4-dimethoxybenzyl)-4-methoxycarbonyl-2-azetidinone

: 84187-64-4
(2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: propylene oxide / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 79 percent / <1.6 molar equiv. K₂S₂O₈, K₂HPO₄ / acetonitrile; H₂O / 2 h / Heating

3: 92 percent / hydrogen / 5percent Pd-C / ethanol / 1 h / Ambient temperature

4: 96 percent / NaHCO₃ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

With dipotassium hydrogenphosphate; dipotassium peroxodisulfate; hydrogen; sodium hydrogencarbonate; methyloxirane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1248/cpb.32.2646

Reference yield:

: 61964-80-5,84187-40-6,86334-62-5,88851-94-9,88851-95-0
cis-1-(2,4-dimethoxybenzyl)-4-methoxycarbonyl-3-phthalimido-2-azetidinone

: 84187-64-4
(2S,3S)-3-{2-[(Z)-Benzyloxyimino]-2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-acetylamino}-4-oxo-azetidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: methylhydrazine / CH₂Cl₂ / 1.) 2 h, r.t; 2.) 8 h, 35 deg C; 3.) r.t

2: propylene oxide / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 79 percent / <1.6 molar equiv. K₂S₂O₈, K₂HPO₄ / acetonitrile; H₂O / 2 h / Heating

4: 92 percent / hydrogen / 5percent Pd-C / ethanol / 1 h / Ambient temperature

5: 96 percent / NaHCO₃ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

With dipotassium hydrogenphosphate; dipotassium peroxodisulfate; hydrogen; sodium hydrogencarbonate; methylhydrazine; methyloxirane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1248/cpb.32.2646