2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate

Base Information

• Chemical Name: 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate
• CAS No.: 78815-21-1
• Molecular Formula: C₂₇H₂₂N₂O₅S
• Molecular Weight: 486.548
• Mol file: 78815-21-1.mol

Synonyms:2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate

Chemical Property of 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate

There total 12 articles about 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate 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: 60.0%

diphenylmethyl (3R,5R,6R)-2-methylene-6-(phenylacetamido)penam-3-carboxylate (139371-97-4) → 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate (78815-21-1)

Guidance literature:

With ozone; In methanol; dichloromethane; at -78 ℃;

DOI:10.1016/0040-4039(91)80130-X

Reference yield: 25.0%

2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl ester (78815-20-0,78855-27-3) → 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate (78815-21-1)

Guidance literature:

With diisopropyl-carbodiimide; In dichloromethane; for 5h; -60 deg C -> r.t.;

DOI:10.1016/S0040-4020(01)92143-X

Reference yield:

Penicillin G sodium (69-57-8) → 2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate (78815-21-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaIO₄ / 1) H₂O; 2) NEt₃, DMF, 20 deg C

2: 65 percent Chromat_. / MgSO₄, (CH₃O)3P / benzene / 40 h / Heating

3: 74 percent / KMnO₄, MgSO₄ / H₂O; ethanol / 15 - 20 °C

4: 1) Triton B / 1) DMF, CH₃OH, -30 deg C, 15 min; 0 deg C, 15 min; 2) DMF, 15 min, -30 deg C; 1 h, 0 deg C; 2 h, r. t.

5: 1) lithium hexamethyldisilazide-ether 1:1 complex / 1) THF, -60 deg C, 30 min; 2) -60 deg C, 30 min, without cooling, 1 h

6: 90 percent / HClO₄ / CH₂Cl₂; methanol; H₂O / 0.5 h / Ambient temperature

7: 25 percent / N,N-diisopropylcarbodiimide / CH₂Cl₂ / 5 h / -60 deg C -> r.t.

With potassium permanganate; sodium periodate; perchloric acid; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; lithium hexamethyldisilazane; diisopropyl-carbodiimide; phosphorous acid trimethyl ester; In methanol; ethanol; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)92143-X

upstream raw materials:

diphenylmethyl (3R,5R,6R)-2-methylene-6-(phenylacetamido)penam-3-carboxylate

2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl ester

Penicillin G sodium

6-β-phenylacetamidopenicillanic acid-(1S)-oxide

Refernces

• 1、 Ghosez,Marchand-Brynaert,Vekemans,et al.. "Synthesis of 2-oxo-penams and penems from penicillin G". . p. 2493 - 2503. Retrieved 2007/10/02.