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

HRID 327352Notes

Reaction equation

HRID 327352 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 LXXI (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 (being eluted with 25% ethyl acetate in hexane) gave 670 mg (Y: 68%) of compound LXXII as a foam.

Workup

  1. washthe organic layer was washed with brine, 10% aqueous HCl
  2. customdried
  3. washSilica gel chromatography (being eluted with 25% ethyl acetate in hexane)
  4. customgave 670 mg (Y: 68%) of compound LXXII as a foam

Sources & evidence

ORD record
ord-f4989d7c15c64ddf8f0593550af48222
Source dataset
uspto-grants-1993_12
Patent number
US05272171

Reaction notes

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