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

Base Information

Chemical Name:benzyl 2-<3β-phenylacetylamino-4β-(4-chloroacetoxy-3-oxobutyl)-2-oxoazetidin-1-yl>-2-triphenylphosphorane-diylethanoate
CAS No.:73935-56-5
Molecular Formula:C₄₄H₄₀ClN₂O₇P
Molecular Weight:775.238
Hs Code.:

Synonyms:

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Chemical Property of benzyl 2-<3β-phenylacetylamino-4β-(4-chloroacetoxy-3-oxobutyl)-2-oxoazetidin-1-yl>-2-triphenylphosphorane-diylethanoate

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Technology Process of benzyl 2-<3β-phenylacetylamino-4β-(4-chloroacetoxy-3-oxobutyl)-2-oxoazetidin-1-yl>-2-triphenylphosphorane-diylethanoate

There total 15 articles about benzyl 2-<3β-phenylacetylamino-4β-(4-chloroacetoxy-3-oxobutyl)-2-oxoazetidin-1-yl>-2-triphenylphosphorane-diylethanoate 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:

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

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

Guidance literature:: Multi-step reaction with 15 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

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 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

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

Guidance literature:: Multi-step reaction with 13 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

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 methanol; dichloromethane; acetic acid;
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

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

Guidance literature:: Multi-step reaction with 11 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

With pyridine; chromium(VI) oxide; hydrogenchloride; thionyl chloride; perchloric acid; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In methanol; dichloromethane; acetic acid;
DOI:10.1248/cpb.28.1563