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

HRID 1656451노트

반응식

HRID 1656451 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 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 (being eluted with 25% ethyl acetate in hexane) gave 670 mg (Y: 68%) of compound XXII 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)

출처 및 근거

ORD 기록
ord-1b7dcddd14644132bfe1186a2d1b9873
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254580

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