7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

Base Information

Chemical Name:7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid
CAS No.:141555-09-1
Molecular Formula:C₂₄H₂₂BrN₅O₁₁S₂
Molecular Weight:700.502
Hs Code.:

7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

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Chemical Property of 7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

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Technology Process of 7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

There total 5 articles about 7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid 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:

: 29126-13-4
3-hydroxymethyl-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

: 141555-09-1
7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

2: 1.) PCl₅, pyridine, 2.) butane-1,3-diol / 1.) CH₂Cl₂, a.) -20 deg C, 15 min, b.) RT, 1.5 h, 2.) CH₂Cl₂, -20 to RT, 1 h

3: 68 percent / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) TFA, anisole, 2.) NH₄OH / 1.) RT, 1 h

With pyridine; dmap; ammonium hydroxide; 1.3-butanediol; phosphorus pentachloride; methoxybenzene; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jm00092a014

Reference yield:

: 122306-86-9
3-bromo-4,5-diacetoxybenzoyl chloride

: 141555-09-1
7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

2: 1.) PCl₅, pyridine, 2.) butane-1,3-diol / 1.) CH₂Cl₂, a.) -20 deg C, 15 min, b.) RT, 1.5 h, 2.) CH₂Cl₂, -20 to RT, 1 h

3: 68 percent / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) TFA, anisole, 2.) NH₄OH / 1.) RT, 1 h

With pyridine; dmap; ammonium hydroxide; 1.3-butanediol; phosphorus pentachloride; methoxybenzene; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jm00092a014

Reference yield:

: 141613-32-3
(6R,7R)-3-(3,4-Diacetoxy-5-bromo-benzoyloxymethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: 141555-09-1
7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-{[(3-bromo-4,5-dihydroxybenzoyl)oxy]methyl}ceph-3-em-4-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) PCl₅, pyridine, 2.) butane-1,3-diol / 1.) CH₂Cl₂, a.) -20 deg C, 15 min, b.) RT, 1.5 h, 2.) CH₂Cl₂, -20 to RT, 1 h

2: 68 percent / CH₂Cl₂ / 1 h / Ambient temperature

3: 1.) TFA, anisole, 2.) NH₄OH / 1.) RT, 1 h

With pyridine; ammonium hydroxide; 1.3-butanediol; phosphorus pentachloride; methoxybenzene; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jm00092a014