(6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester
CAS No.:73910-36-8
Molecular Formula:C₂₄H₂₄N₂O₄
Molecular Weight:404.466
Hs Code.:

Synonyms:

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Chemical Property of (6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

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Technology Process of (6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

There total 16 articles about (6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-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:

: 73910-32-4
benzyl 7β-phenylacetylamino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-carba-1-dethia-3-cephem-4-carboxylate

: 73910-36-8
(6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

: 73910-37-9
benzyl 7β-phenylacetylamino-3-methyl-1-carba-1-dethia-3-cephem-4-carboxylate

Guidance literature:: With magnesium; In dichloromethane; acetic acid; at 10 - 20 ℃; for 5h;
DOI:10.1248/cpb.28.1563

Reference yield:

: 4052-69-1
penicillin-V β-sulfoxide benzyl ester

: 73910-36-8
(6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 131 g / trimethylphosphite, molecular sieves / toluene / 2 h / Heating

2: 48 g / 0.5N HCl / methanol / 0.25 h / Heating

3: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

4: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

5: Et₃N / CH₂Cl₂ / -78 °C

6: 10 g / Et₃N / 2 h / Ambient temperature

7: Zn / CH₂Cl₂; acetic acid

8: 2.3 g / pyridine / 0.17 h

9: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

10: 17.4 g / n-BuLi / tetrahydrofuran; hexane / 6 h / Ambient temperature

11: 11.8 g / CrO₃ / acetone / 0.25 h / Ambient temperature

12: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C, 40 min

13: SOCl₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

14: 8.81 g / CH₂Cl₂ / 1 h / Heating

15: 60 percent / dioxane / 10 h / Heating

16: 135 mg / Mg / CH₂Cl₂; acetic acid / 5 h / 10 - 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; n-butyllithium; thionyl chloride; molecular sieve; 4 A molecular sieve; phosphorus pentachloride; sodium hydrogencarbonate; ozone; magnesium; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid; acetone; toluene;
DOI:10.1248/cpb.28.1563

Reference yield:

: 68047-66-5
(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester

: 73910-36-8
(6R,7S)-3-Methylene-8-oxo-7-phenylacetylamino-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

2: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

3: Et₃N / CH₂Cl₂ / -78 °C

4: 10 g / Et₃N / 2 h / Ambient temperature

5: Zn / CH₂Cl₂; acetic acid

6: 2.3 g / pyridine / 0.17 h

7: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

8: 17.4 g / n-BuLi / tetrahydrofuran; hexane / 6 h / Ambient temperature

9: 11.8 g / CrO₃ / acetone / 0.25 h / Ambient temperature

10: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C, 40 min

11: SOCl₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

12: 8.81 g / CH₂Cl₂ / 1 h / Heating

13: 60 percent / dioxane / 10 h / Heating

14: 135 mg / Mg / CH₂Cl₂; acetic acid / 5 h / 10 - 20 °C

With pyridine; chromium(VI) oxide; methanol; n-butyllithium; thionyl chloride; 4 A molecular sieve; phosphorus pentachloride; sodium hydrogencarbonate; ozone; magnesium; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; acetic acid; acetone;
DOI:10.1248/cpb.28.1563