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

Base Information

Chemical Name:7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid
CAS No.:72292-42-3
Molecular Formula:C₂₃H₂₅N₅O₇
Molecular Weight:483.481
Hs Code.:

Synonyms:

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

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

There total 16 articles about 7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-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: 93.0%

: 72292-40-1,72345-50-7,72377-68-5
7β-<(2R)-2-phenyl-2-amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 72292-42-3,72401-86-6
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid

Guidance literature:: DOI:10.1248/cpb.28.1563

Reference yield:

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

: 72292-42-3,72401-86-6
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid

Guidance literature:: Multi-step reaction with 16 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: NaIO₄, 1N H₂SO₄ / tetrahydrofuran / 1 h

12: 375 mg / Ambient temperature

13: 1.) PCl₅, 2.) MeOH

14: 92 percent / EEDQ / tetrahydrofuran

15: 66 percent / AlCl₃

16: 93 percent

With pyridine; hydrogenchloride; methanol; sodium periodate; aluminium trichloride; thionyl chloride; perchloric acid; phosphorus pentachloride; sulfuric acid; toluene-4-sulfonic acid; ozone; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; acetic acid;
DOI:10.1248/cpb.28.1563

Reference yield:

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

: 72292-42-3,72401-86-6
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / EEDQ / tetrahydrofuran

2: 66 percent / AlCl₃

3: 93 percent

With aluminium trichloride; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In tetrahydrofuran;
DOI:10.1248/cpb.28.1563