diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

Base Information

Chemical Name:diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate
CAS No.:159492-50-9
Molecular Formula:C₃₂H₃₀N₆O₈S₂
Molecular Weight:690.758
Hs Code.:

Synonyms:diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

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Chemical Property of diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

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Technology Process of diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

There total 3 articles about diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate 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: 92.0%

: (Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetyl chloride hydrochloride

: 159492-82-7
diphenylmethyl 7β-amino-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

: 159492-50-9
diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

Guidance literature:: diphenylmethyl 7β-amino-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 20 ℃; for 0.416667h;

(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetyl chloride hydrochloride; In dichloromethane; at 5 ℃; for 4h;
DOI:10.1016/S0968-0896(99)00257-6

Reference yield:

: (E)-1-tri(n-butyl)stannyl-4-carbamoyloxy-1-butene

: 159492-50-9
diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 22 percent / LiBr; 2-tri(n-butyl)stannyl-4-carbamoyloxy-1-butene / Pd(CH₃CN)2Cl₂ / dimethylformamide / 15 h / 5 - 20 °C

2.1: 90 percent / conc. HCl / methanol / 4 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / CH₂Cl₂ / 0.42 h / 20 °C

3.2: 92 percent / CH₂Cl₂ / 4 h / 5 °C

With hydrogenchloride; N,O-bis-(trimethylsilyl)-acetamide; 2-tri(n-butyl)stannyl-4-carbamoyloxy-1-butene; lithium bromide; dichloro bis(acetonitrile) palladium(II); In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: coupling / 2.1: Hydrolysis / 3.1: silylation / 3.2: Acylation;
DOI:10.1016/S0968-0896(99)00257-6

Reference yield:

: 159492-80-5
diphenylmethyl 7β-formamido-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

: 159492-50-9
diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(E)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / conc. HCl / methanol / 4 h / 20 °C

2.1: N,O-bis(trimethylsilyl)acetamide / CH₂Cl₂ / 0.42 h / 20 °C

2.2: 92 percent / CH₂Cl₂ / 4 h / 5 °C

With hydrogenchloride; N,O-bis-(trimethylsilyl)-acetamide; In methanol; dichloromethane; 1.1: Hydrolysis / 2.1: silylation / 2.2: Acylation;
DOI:10.1016/S0968-0896(99)00257-6