(6R,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (6R,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS No.: 76284-35-0
• Molecular Formula: C₃₄H₄₁ClN₂O₇
• Molecular Weight: 625.162

Synonyms:

Chemical Property of (6R,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-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,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 18 articles about (6R,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-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,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (76284-35-0)

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: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

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

12: SOCl₂, pyridine / CH₂Cl₂

13: 1.58 g / CH₂Cl₂ / Heating

14: 956 mg / 10percent HCl / methanol / 1 h / Ambient temperature

15: 1.) pyridine, 2.) CrO₃ / 1.) CH₂Cl₂, ice-aceton cooling, 2 h, 2.) acetone, 0 deg C to r.t., 45 min

16: 60 percent / dioxane / 24 h / Heating

17: 1.) PCl₅, 2.) MeOH

18: 2.) nickel peroxide / 1.) CH₂Cl₂, reflux, 2.) CH₂Cl₂, -20 deg C, 0 deg C

19: 160 mg

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; nickel(IV) oxide; thionyl chloride; perchloric acid; molecular sieve; 4 A molecular sieve; phosphorus pentachloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; In 1,4-dioxane; methanol; dichloromethane; acetic acid; 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,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (76284-35-0)

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: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

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

10: SOCl₂, pyridine / CH₂Cl₂

11: 1.58 g / CH₂Cl₂ / Heating

12: 956 mg / 10percent HCl / methanol / 1 h / Ambient temperature

13: 1.) pyridine, 2.) CrO₃ / 1.) CH₂Cl₂, ice-aceton cooling, 2 h, 2.) acetone, 0 deg C to r.t., 45 min

14: 60 percent / dioxane / 24 h / Heating

15: 1.) PCl₅, 2.) MeOH

16: 2.) nickel peroxide / 1.) CH₂Cl₂, reflux, 2.) CH₂Cl₂, -20 deg C, 0 deg C

17: 160 mg

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; nickel(IV) oxide; thionyl chloride; perchloric acid; 4 A molecular sieve; phosphorus pentachloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In 1,4-dioxane; methanol; dichloromethane; acetic acid;

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,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (76284-35-0)

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: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

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

8: SOCl₂, pyridine / CH₂Cl₂

9: 1.58 g / CH₂Cl₂ / Heating

10: 956 mg / 10percent HCl / methanol / 1 h / Ambient temperature

11: 1.) pyridine, 2.) CrO₃ / 1.) CH₂Cl₂, ice-aceton cooling, 2 h, 2.) acetone, 0 deg C to r.t., 45 min

12: 60 percent / dioxane / 24 h / Heating

13: 1.) PCl₅, 2.) MeOH

14: 2.) nickel peroxide / 1.) CH₂Cl₂, reflux, 2.) CH₂Cl₂, -20 deg C, 0 deg C

15: 160 mg

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; nickel(IV) oxide; thionyl chloride; perchloric acid; phosphorus pentachloride; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In 1,4-dioxane; methanol; dichloromethane; acetic acid;

DOI:10.1248/cpb.28.1563

upstream raw materials:

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

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

Downstream raw materials:

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

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