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

HRID 327352노트

반응식

HRID 327352 반응식
[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

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4989d7c15c64ddf8f0593550af48222
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272171

반응 노트

불러오는 중…