3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham

Base Information

• Chemical Name: 3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham
• CAS No.: 99828-79-2
• Molecular Formula: C₂₄H₂₄BrN₃O₈S
• Molecular Weight: 594.44

Synonyms:3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham

Chemical Property of 3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham

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Technology Process of 3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham

There total 2 articles about 3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham 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: 87.0%

4-nitro-benzoyl chloride (122-04-3) + 3α-bromo-3β-methyl-4β-(hydroxymethyl)-4α-methoxy-7β-(phenoxyacetamido)cepham (99881-82-0) → 3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham (99828-79-2)

Guidance literature:

With pyridine; for 1h; Ambient temperature;

DOI:10.1021/jo00354a028

Reference yield: 3.3%

methanol (67-56-1) + 3-methyl-4-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)-3-cephem (132645-19-3) → 4-Nitro-benzoic acid (2S,3S,7R)-3-bromo-2-methoxy-3-methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester (99809-77-5,99828-79-2) + 4-Nitro-benzoic acid (2S,3R,7R)-3-bromo-2-methoxy-3-methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester + (4S,2'S)-3β-bromo-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-<2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane>cepham (132645-20-6,132746-29-3) + (4S,2'R)-3β-bromo-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-<2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane>cepham (132645-20-6,132746-29-3)

Guidance literature:

With bromine; calcium carbonate; at 0 ℃; for 0.5h; Product distribution;

DOI:10.1021/jo00006a035

Reference yield: 90.0%

silver(I) acetate (563-63-3) + 4-Nitro-benzoic acid (2S,3S,7R)-3-bromo-2-methoxy-3-methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester (99809-77-5,99828-79-2) → 4-Nitro-benzoic acid (2S,3S,6R)-3-acetoxymethyl-2-methoxy-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ylmethyl ester (99809-78-6,99809-79-7)

Guidance literature:

In methanol; at 60 ℃; for 24h;

DOI:10.1021/jo00006a035

upstream raw materials:

methanol

3-methyl-4-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)-3-cephem

4-nitro-benzoyl chloride

3α-bromo-3β-methyl-4β-(hydroxymethyl)-4α-methoxy-7β-(phenoxyacetamido)cepham

Downstream raw materials:

4-Nitro-benzoic acid (2S,3S,6R)-3-acetoxymethyl-2-methoxy-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ylmethyl ester

3-methyl-4α-methoxy-4β-<<(p-nitrobenzoyl)oxy>methyl>-7β-(phenoxyacetamido)-2-cephem

2α-(acetoxymethyl)-2β-methyl-3α-methoxy-3β-<((p-nitrobenzoyl)oxy)methyl>-6β-(phenoxyacetamido)penam

2α-(acetoxymethyl)-2β-methyl-3α-methoxy-3β-<((p-nitrobenzoyl)oxy)methyl>-6β-(phenoxyacetamido)penam (S)-sulfoxide

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