Réaction #62560

ord-16963ddea0f6455db41136801f58d750

Équation de réaction

[Na+].[OH-]
NaOH
C=CCOC(=O)Cl
chloroformic acid allyl ester
COc1ccc(CN2C(=O)[C@H]([C@@H](C)O)[C@H]2C(=O)OC(C)(C)C)cc1
(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone
C=CCOC(=O)Cl
chloroformic acid allyl ester
→
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N(Cc2ccc(OC)cc2)[C@@H]1C(=O)OC(C)(C)C
title compound
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N(Cc2ccc(OC)cc2)[C@@H]1C(=O)OC(C)(C)C
(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-tert.-butoxycarbonyl-2-azetidinone

Réactifs

[Na+].[OH-]
NaOH
C=CCOC(=O)Cl
chloroformic acid allyl ester
COc1ccc(CN2C(=O)[C@H]([C@@H](C)O)[C@H]2C(=O)OC(C)(C)C)cc1
(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone
—
20
C=CCOC(=O)Cl
chloroformic acid allyl ester

Réactifs

CCCC[N+](CCCC)(CCCC)CCCC.O=S(=O)([O-])O
tetrabutylammonium bisulphate

Solvants

ClCCl
methylene chloride
ClCCl
methylene chloride

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe aqueous phase is separated off
  2. 2
    Lavagethe organic layer is washed in succession with 5% aqueous citric acid and 8% aqueous NaHCO3 solution
  3. 3
    Autredried
  4. 4
    Concentrationconcentrated by evaporation
  5. 5
    AutreAfter purifying by chromatography

Mode opératoire

At 0°, 24 ml of 1N NaOH, 820 mg of tetrabutylammonium bisulphate and 1 ml of chloroformic acid allyl ester are added to a solution of 2 g of (3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone in 24 ml of methylene chloride and the whole is stirred vigorously. After a reaction time of 20 and 40 minutes, further portions (each of 1 ml) of chloroformic acid allyl ester are added. The reaction mixture is diluted with methylene chloride, the aqueous phase is separated off and the organic layer is washed in succession with 5% aqueous citric acid and 8% aqueous NaHCO3 solution and then dried and concentrated by evaporation. After purifying by chromatography, the pure, amorphous title compound is obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04761408uspto-grants-1988_08