6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

Base Information

• Chemical Name: 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
• CAS No.: 483340-24-5
• Molecular Formula: C₂₃H₂₄BrNO₆S
• Molecular Weight: 522.417

Synonyms:6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

Chemical Property of 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

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Technology Process of 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

There total 2 articles about 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl 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: 69.0%

6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (91618-40-5) → 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-24-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/S0014-827X(02)01261-2

Reference yield:

diphenylmethyl 6,6-dibromopenicillanate (75527-84-3) → 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MeMgBr / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

1.2: 68 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

2.1: 69 percent / mCPBA / CH₂Cl₂ / 20 h / 20 °C

With methylmagnesium bromide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0014-827X(02)01261-2

upstream raw materials:

6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

diphenylmethyl 6,6-dibromopenicillanate

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