Sodium Hydroxide → (3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-tert.-butoxycarbonyl-2-azetidinone

HRID 34282

Reaction equation

HRID 34282 reaction equation
[OH-].[Na+].[CH2:3]([O:6][C:7](Cl)=[O:8])[CH:4]=[CH2:5].[CH3:10][O:11][C:12]1[CH:33]=[CH:32][C:15]([CH2:16][N:17]2[C@H:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:19]([C@H:28]([OH:30])[CH3:29])[C:18]2=[O:31])=[CH:14][CH:13]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[C@H:20]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C@@H:19]([C@H:28]([O:30][C:7]([O:6][CH2:3][CH:4]=[CH2:5])=[O:8])[CH3:29])[C:18]2=[O:31])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformate2×HCID 18604778(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone

Product 1

HCID 18604780(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-tert.-butoxycarbonyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  1. customthe aqueous phase is separated off
  2. washthe organic layer is washed in succession with 5% aqueous citric acid and 8% aqueous NaHCO3 solution
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customAfter purifying by chromatography

Sources & evidence

ORD record
ord-16963ddea0f6455db41136801f58d750
Source dataset
uspto-grants-1988_08
Patent number
US04761408

Linked notes

Loading…