(6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS No.: 74560-22-8
• Molecular Formula: C₂₃H₂₃N₅O₇S
• Molecular Weight: 513.531
• Mol file: 74560-22-8.mol

Synonyms:

Chemical Property of (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 11 articles about (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl 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:

2-[(S)-3-Amino-2-(2-hydroxy-ethoxy)-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester (72217-21-1,72217-22-2) → (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (74560-22-8)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 1.33 h / 0 °C

2: 1.) O₃, 2.) aq. NaHSO₃ / 1.) AcOEt, from -65 to 0 deg C, 2.) AcOEt

3: 9.46 g / Zn, AcOH / CH₂Cl₂ / 2 h / 5 °C

4: 2,6-lutidine, SOCl₂ / CH₂Cl₂ / 1 h / 0 °C

5: CH₂Cl₂ / 4 h / Heating

6: 1 N aq. NaOH / methanol / 0.25 h

7: 74 percent / pyridine, dicyclohexylcarbodiimide (DCC), DMSO, TFA / benzene / Ambient temperature

8: 1.) N,N-dimethylaniline, PCl₅, 2.) MeOH / 1.) CH₂Cl₂, -35 deg C, 2 h, 2.) CH₂Cl₂, from -50 to 0 deg C, 80 min

9: 1.) DMF-POCl₃, 2.) pyridine / 1.) AcOEt, 0 deg C, 70 min, 2.) AcOEt, from -50 to 0 deg C, 70 min

With pyridine; 2,6-dimethylpyridine; methanol; sodium hydroxide; thionyl chloride; phosphorus pentachloride; ozone; sodium hydrogensulfite; acetic acid; dimethyl sulfoxide; N,N-dimethyl-aniline; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; trichlorophosphate; In methanol; dichloromethane; benzene;

DOI:10.1021/jm00184a009

Reference yield:

1,2-secopenicillin tosylate (74280-93-6) → (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (74560-22-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 65 percent / Cl₂ / CH₂Cl₂; CCl₄ / 1 h / -65 °C

2: AgBF₄ / CH₂Cl₂ / 2.08 h / -45 - 0 °C

3: pyridine / 1.33 h / 0 °C

4: 1.) O₃, 2.) aq. NaHSO₃ / 1.) AcOEt, from -65 to 0 deg C, 2.) AcOEt

5: 9.46 g / Zn, AcOH / CH₂Cl₂ / 2 h / 5 °C

6: 2,6-lutidine, SOCl₂ / CH₂Cl₂ / 1 h / 0 °C

7: CH₂Cl₂ / 4 h / Heating

8: 1 N aq. NaOH / methanol / 0.25 h

9: 74 percent / pyridine, dicyclohexylcarbodiimide (DCC), DMSO, TFA / benzene / Ambient temperature

10: 1.) N,N-dimethylaniline, PCl₅, 2.) MeOH / 1.) CH₂Cl₂, -35 deg C, 2 h, 2.) CH₂Cl₂, from -50 to 0 deg C, 80 min

11: 1.) DMF-POCl₃, 2.) pyridine / 1.) AcOEt, 0 deg C, 70 min, 2.) AcOEt, from -50 to 0 deg C, 70 min

With pyridine; 2,6-dimethylpyridine; methanol; sodium hydroxide; silver tetrafluoroborate; thionyl chloride; phosphorus pentachloride; chlorine; ozone; sodium hydrogensulfite; acetic acid; dimethyl sulfoxide; N,N-dimethyl-aniline; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; trichlorophosphate; In methanol; tetrachloromethane; dichloromethane; benzene;

DOI:10.1021/jm00184a009

Reference yield:

benzyl 2-[2-oxo-3β-phenoxyacetamido-4β-(2-phenoxyacetoxyethoxy)azetidin-1-yl]glyoxylate (74560-15-9) → (6R,7S)-7-{2-(2-Formylamino-thiazol-4-yl)-2-[(Z)-isopropoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (74560-22-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 9.46 g / Zn, AcOH / CH₂Cl₂ / 2 h / 5 °C

2: 2,6-lutidine, SOCl₂ / CH₂Cl₂ / 1 h / 0 °C

3: CH₂Cl₂ / 4 h / Heating

4: 1 N aq. NaOH / methanol / 0.25 h

5: 74 percent / pyridine, dicyclohexylcarbodiimide (DCC), DMSO, TFA / benzene / Ambient temperature

6: 1.) N,N-dimethylaniline, PCl₅, 2.) MeOH / 1.) CH₂Cl₂, -35 deg C, 2 h, 2.) CH₂Cl₂, from -50 to 0 deg C, 80 min

7: 1.) DMF-POCl₃, 2.) pyridine / 1.) AcOEt, 0 deg C, 70 min, 2.) AcOEt, from -50 to 0 deg C, 70 min

With pyridine; 2,6-dimethylpyridine; methanol; sodium hydroxide; thionyl chloride; phosphorus pentachloride; acetic acid; dimethyl sulfoxide; N,N-dimethyl-aniline; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; trichlorophosphate; In methanol; dichloromethane; benzene;

DOI:10.1021/jm00184a009

upstream raw materials:

2-isopropoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid

(6R,7S)-7-Amino-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

2-[(S)-3-Amino-2-(2-hydroxy-ethoxy)-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester

1,2-secopenicillin tosylate