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

Base Information

• Chemical Name: 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
• CAS No.: 73910-43-7
• Molecular Formula: C₂₄H₂₇N₅O₈
• Molecular Weight: 513.507
• Mol file: 73910-43-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 18 articles about 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 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:

(R)-3-Methyl-2-pent-4-en-(Z)-ylideneamino-but-3-enoic acid benzyl ester (73910-25-5) → 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 (73910-43-7)

Guidance literature:

Multi-step reaction with 18 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

16: 90 percent / EEDQ / tetrahydrofuran

17: 38 percent / AlCl₃, anisole / nitromethane

18: 15 mg / propylene oxide, BSA / acetonitrile

With pyridine; chromium(VI) oxide; methanol; benzenesulfonamide; n-butyllithium; aluminium trichloride; thionyl chloride; phosphorus pentachloride; water; ozone; magnesium; acetic acid; methoxybenzene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; 3-chloro-benzenecarboperoxoic acid; methyloxirane; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; nitromethane; hexane; dichloromethane; acetic acid; ethyl acetate; acetone; acetonitrile;

DOI:10.1248/cpb.28.1563

Reference yield:

2-((2R,3S)-3-Amino-2-but-3-enyl-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic 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 (73910-43-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 2.3 g / pyridine / 0.17 h

2: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

3: 17.4 g / n-BuLi / tetrahydrofuran; hexane / 6 h / Ambient temperature

4: 11.8 g / CrO₃ / acetone / 0.25 h / Ambient temperature

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

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

7: 8.81 g / CH₂Cl₂ / 1 h / Heating

8: 60 percent / dioxane / 10 h / Heating

9: 135 mg / Mg / CH₂Cl₂; acetic acid / 5 h / 10 - 20 °C

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

11: 188 mg / diethyl ether; ethyl acetate; CH₂Cl₂ / 3 h / Ambient temperature

12: 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

13: 90 percent / EEDQ / tetrahydrofuran

14: 38 percent / AlCl₃, anisole / nitromethane

15: 15 mg / propylene oxide, BSA / acetonitrile

With pyridine; chromium(VI) oxide; methanol; benzenesulfonamide; n-butyllithium; aluminium trichloride; thionyl chloride; phosphorus pentachloride; water; ozone; magnesium; acetic acid; methoxybenzene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 3-chloro-benzenecarboperoxoic acid; methyloxirane; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; nitromethane; hexane; dichloromethane; acetic acid; ethyl acetate; acetone; acetonitrile;

DOI:10.1248/cpb.28.1563

Reference yield:

(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) → 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 (73910-43-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / EEDQ / tetrahydrofuran

2: 38 percent / AlCl₃, anisole / nitromethane

3: 15 mg / propylene oxide, BSA / acetonitrile

With benzenesulfonamide; aluminium trichloride; methoxybenzene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; methyloxirane; In tetrahydrofuran; nitromethane; acetonitrile;

DOI:10.1248/cpb.28.1563

upstream raw materials:

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

4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

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

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

Refernces