Imidazole → (3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one

HRID 2260765Notes

Reaction equation

HRID 2260765 reaction equation
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].N1[CH:10]=[CH:9]N=C1.[CH2:11]([Si:13](Cl)([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12].C(OCC)(=[O:21])C.[CH2:25]1[CH2:29]O[CH2:27][CH2:26]1>>[C:10]1([C@@H:4]2[NH:1][C:2](=[O:5])[C@@H:3]2[O:21][Si:13]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:11][CH3:12])[CH:9]=[CH:27][CH:26]=[CH:25][CH:29]=1

Participants

6

Reactant 5

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 13819ChlorotriethylsilaneHCID 1367212-Azetidinone

Product 1

HCID 10826417(3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one

Procedure

To azetidinone XXI (580 mg, 3.55 mmol) in dry THF (5.0 mL) was added imidazole (265.5 mg, 3.90 mmol), followed by triethylsilyl chloride (TESCl, 0.654 mL, 3.90 mmol). The mixture was allowed to be stirred for 1 h. Ethyl acetate was added and the organic layer was washed with brine, 10% aqueous HCl and dried. Silica gel chromatography (eluted with 25% ethyl acetate in hexane) gave 670 mg (Y: 68%) of compound XXII as a foam. ##STR11##

Workup

  1. washthe organic layer was washed with brine, 10% aqueous HCl
  2. customdried
  3. washSilica gel chromatography (eluted with 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f35573e0998e455c85e18c798802b62b
Source dataset
uspto-grants-1995_12
Patent number
US05478854

Reaction notes

Loading…