3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester
• CAS No.: 33465-36-0
• Molecular Formula: C₁₇H₁₈N₂O₄S
• Molecular Weight: 346.407

Synonyms:3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester

Chemical Property of 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester

There total 16 articles about 3-methyl-7β-phenylacetamidoceph-3-em-4-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:

(6R)-7t-amino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester (37850-83-2,49626-64-4,51020-69-0) + phenylacetyl chloride (103-80-0) → methyl 7β-phenylacetamido-3-methylceph-3-em-4-carboxylate (33465-36-0,72368-42-4)

Guidance literature:

With triethylamine; at 0 - 20 ℃;

Reference yield:

(R)-2-[(2R)-2-(N,N'-bis-methoxycarbonyl-hydrazinosulfanyl)-4-oxo-3c-(2-phenyl-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester (61959-79-3) → 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester (33465-36-0)

Guidance literature:

With potassium hydroxide; In benzene;

DOI:10.1021/ja00443a047

Reference yield:

methyl (2R)-<(3S,4R)-4-(benzothiazol-2-yldithio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-3-enoate (62284-24-6) → 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester (33465-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / MgBr₂ / acetonitrile; tetrahydrofuran; H₂O / 25 °C / Pt electrodes, 10 mA/cm2

2: dimethylformamide / Ambient temperature

3: Al₂O₃ / benzene; ethyl acetate

With aluminum oxide; magnesium bromide; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1246/cl.1982.1829

upstream raw materials:

methyl 6β-(phenylacetamido)penicillanate 1β-oxide

(R)-2-[(2R)-2-(N,N'-bis-methoxycarbonyl-hydrazinosulfanyl)-4-oxo-3c-(2-phenyl-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester

1β-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid N,N'-diisopropyl-hydrazide

1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid methyl ester

Downstream raw materials:

(5R)-2-isopropenyl-7-oxo-6t-(2-phenyl-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c,3t-dicarboxylic acid 3-ethyl ester 2-methyl ester

2-(2-benzyl-thiazole-4-carbonylamino)-4-methoxy-3-methyl-but-2-enoic acid methyl ester

2-(2-benzyl-thiazole-4-carbonylamino)-2-methoxy-3-methyl-but-3-enoic acid methyl ester

2-(2-benzyl-thiazole-4-carbonylamino)-4-ethoxy-3-methyl-but-2-enoic acid methyl ester

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