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

Base Information

• Chemical Name: 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
• CAS No.: 483340-41-6
• Molecular Formula: C₂₃H₂₂BrNO₄S
• Molecular Weight: 488.402
• Mol file: 483340-41-6.mol

Synonyms:6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

Chemical Property of 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester

There total 2 articles about 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-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: 95.0%

6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-23-4) → 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-41-6)

Guidance literature:

With dipyridinium dichromate; molecular sieve; In dichloromethane; at 20 ℃; for 18h;

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

Reference yield:

diphenylmethyl 6,6-dibromopenicillanate (75527-84-3) → 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-41-6)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 31 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

2.1: 95 percent / PDC; activated molecular sieves / CH₂Cl₂ / 18 h / 20 °C

With dipyridinium dichromate; molecular sieve; methylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;

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

Reference yield: 72.0%

N-methoxylamine hydrochloride (593-56-6) + 6α-acetyl-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-41-6) → 6β-bromo-6α-(1-methoxyiminoethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester (483340-28-9)

Guidance literature:

With pyridine; sodium sulfate; In dichloromethane; at 20 ℃; for 120h;

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

upstream raw materials:

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

diphenylmethyl 6,6-dibromopenicillanate

Downstream raw materials:

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