(6R,7S)-7-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (6R,7S)-7-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS No.: 73910-41-5
• Molecular Formula: C₁₆H₁₈N₂O₄
• Molecular Weight: 302.33

Synonyms:(6R,7S)-7-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Chemical Property of (6R,7S)-7-Amino-3-methoxy-8-oxo-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-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 19 articles about (6R,7S)-7-Amino-3-methoxy-8-oxo-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:

penicillin-V β-sulfoxide benzyl ester (4052-69-1) → (6R,7S)-7-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73910-41-5)

Guidance literature:

Multi-step reaction with 19 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

17: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, 0 deg C, 10 min

18: 188 mg / diethyl ether; ethyl acetate; CH₂Cl₂ / 3 h / Ambient temperature

19: 1.) PCl₅, 2.) MeOH, 3.) H₂O / 1.) CH₂Cl₂, pyridine, -25 deg C to r.t., 30 min, 2.) -30 deg C, 20 min, 3.) -20 deg C, 10 min; r.t., 30 min

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; n-butyllithium; thionyl chloride; molecular sieve; 4 A molecular sieve; phosphorus pentachloride; water; sodium hydrogencarbonate; ozone; magnesium; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; acetic acid; ethyl acetate; acetone; toluene;

DOI:10.1248/cpb.28.1563

Reference yield:

(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester (68047-66-5) → (6R,7S)-7-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73910-41-5)

Guidance literature:

Multi-step reaction with 17 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

15: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, 0 deg C, 10 min

16: 188 mg / diethyl ether; ethyl acetate; CH₂Cl₂ / 3 h / Ambient temperature

17: 1.) PCl₅, 2.) MeOH, 3.) H₂O / 1.) CH₂Cl₂, pyridine, -25 deg C to r.t., 30 min, 2.) -30 deg C, 20 min, 3.) -20 deg C, 10 min; r.t., 30 min

With pyridine; chromium(VI) oxide; methanol; n-butyllithium; thionyl chloride; 4 A molecular sieve; phosphorus pentachloride; water; sodium hydrogencarbonate; ozone; magnesium; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; acetic acid; ethyl acetate; acetone;

DOI:10.1248/cpb.28.1563

Reference yield:

(R)-3-Methyl-2-pent-4-en-(Z)-ylideneamino-but-3-enoic acid benzyl ester (73910-25-5) → (6R,7S)-7-Amino-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73910-41-5)

Guidance literature:

Multi-step reaction with 15 steps

1: Et₃N / CH₂Cl₂ / -78 °C

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

3: Zn / CH₂Cl₂; acetic acid

4: 2.3 g / pyridine / 0.17 h

5: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

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

7: 11.8 g / CrO₃ / acetone / 0.25 h / Ambient temperature

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

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

10: 8.81 g / CH₂Cl₂ / 1 h / Heating

11: 60 percent / dioxane / 10 h / Heating

12: 135 mg / Mg / CH₂Cl₂; acetic acid / 5 h / 10 - 20 °C

13: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, 0 deg C, 10 min

14: 188 mg / diethyl ether; ethyl acetate; CH₂Cl₂ / 3 h / Ambient temperature

15: 1.) PCl₅, 2.) MeOH, 3.) H₂O / 1.) CH₂Cl₂, pyridine, -25 deg C to r.t., 30 min, 2.) -30 deg C, 20 min, 3.) -20 deg C, 10 min; r.t., 30 min

With pyridine; chromium(VI) oxide; methanol; n-butyllithium; thionyl chloride; phosphorus pentachloride; water; ozone; magnesium; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; acetic acid; ethyl acetate; acetone;

DOI:10.1248/cpb.28.1563

upstream raw materials:

benzyl 7β-phenylacetylamino-3-methoxy-1-carba-1-dethia-3-cephem-4-carboxylate

penicillin-V β-sulfoxide benzyl ester

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

(R)-3-Methyl-2-pent-4-en-(Z)-ylideneamino-but-3-enoic acid benzyl ester

Downstream raw materials:

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazin-1-yl-carbonyl)amino>acetylamino-3-methoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid

7β-<(2R)-2-phenyl-2-amino>acetylamino-3-methoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid

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