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

Base Information

• Chemical Name: 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl ester
• CAS No.: 78815-20-0
• Molecular Formula: C₂₇H₂₄N₂O₆S
• Molecular Weight: 504.563
• Mol file: 78815-20-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl 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: 90.0%

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-benzhydryl malonate (78815-19-7,78855-21-7) → 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl ester (78815-20-0,78855-27-3)

Guidance literature:

With perchloric acid; In methanol; dichloromethane; water; for 0.5h; Ambient temperature;

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

Reference yield:

Penicillin G sodium (69-57-8) → 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl ester (78815-20-0,78855-27-3)

Guidance literature:

Multi-step reaction with 6 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

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

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

Reference yield:

6-β-phenylacetamidopenicillanic acid-(1S)-oxide (54275-92-2) → 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzhydryl ester (78815-20-0,78855-27-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent Chromat_. / MgSO₄, (CH₃O)3P / benzene / 40 h / Heating

2: 74 percent / KMnO₄, MgSO₄ / H₂O; ethanol / 15 - 20 °C

3: 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.

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

5: 90 percent / HClO₄ / CH₂Cl₂; methanol; H₂O / 0.5 h / Ambient temperature

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

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

upstream raw materials:

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-benzhydryl malonate

Penicillin G sodium

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

diphenylmethyl bromoacetate

Downstream raw materials:

2-oxo-bisnorpenicillin G-3-benzhydryl carboxylate

Refernces