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

Base Information

Chemical Name:benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate
CAS No.:73935-57-6
Molecular Formula:C₂₆H₂₅ClN₂O₆
Molecular Weight:496.947
Hs Code.:

Synonyms:

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Chemical Property of benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate

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Technology Process of benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate

There total 16 articles about benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate 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: 60.0%

: 73935-56-5
benzyl 2-<3β-phenylacetylamino-4β-(4-chloroacetoxy-3-oxobutyl)-2-oxoazetidin-1-yl>-2-triphenylphosphorane-diylethanoate

: 73935-57-6
benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate

Guidance literature:: In 1,4-dioxane; for 24h; Heating;
DOI:10.1248/cpb.28.1563

Reference yield:

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

: 73935-57-6
benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate

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: 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

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; 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:

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

: 73935-57-6
benzyl 7β-phenylacetylamino-3-chloroacetoxymethyl-1-carba-1-dethia-3-cephem-4-carboxylate

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: 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

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; 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