(2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 101760-73-0
• Molecular Formula: C₃₇H₃₄N₂O₅S
• Molecular Weight: 618.753

Synonyms:(2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

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Technology Process of (2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 2 articles about (2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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:

diphenylmethyl 6β-(2-phenylacetamido)penicillanate (67565-52-0) → (2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (101760-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine, PCl₅ / benzene / 1 h / 0 °C

2: toluene / 1.5 h / 55 - 60 °C

With pyridine; phosphorus pentachloride; In toluene; benzene;

DOI:10.1021/jo00360a030

Reference yield:

sodium phenylacetate (114-70-5) + (2S,5R,6R)-6-[1-Chloro-2-phenyl-eth-(Z)-ylideneamino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester → (2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (101760-73-0)

Guidance literature:

In toluene; at 55 - 60 ℃; for 1.5h; Yield given;

DOI:10.1021/jo00360a030

Reference yield: 52.0%

(2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (101760-73-0) → (2S,4R,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (101760-76-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In benzene; for 0.5h; Ambient temperature;

DOI:10.1021/jo00360a030

upstream raw materials:

sodium phenylacetate

diphenylmethyl 6β-(2-phenylacetamido)penicillanate

Downstream raw materials:

(2S,4R,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

benzyl 6β-(phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxylate 1α-S-oxide

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