Imidazole → tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 1436109

반응식

HRID 1436109 반응식
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][C@H:20]([CH3:39])[C@H:21]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=1.N1C=CN=C1.C(OCC)(=O)C>CN(C=O)C>[Si:5]([O:19][C@H:20]([CH3:39])[C@H:21]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

생성물 1

HCID 68718850tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Tert-Butylchlorodiphenylsilane (2.0 ml) was added in four portions to a solution of tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate (610 mg) and imidazole (817 mg) in DMF (3 ml) in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for three hours. Ethyl acetate was added to the reaction solution, which was then sequentially washed with water, 1 N hydrochloric acid, water, a saturated sodium bicarbonate solution, and brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:diethyl ether 49:1 to 19:1) to obtain 684 mg of the title compound.

후처리

  1. washwas then sequentially washed with water, 1 N hydrochloric acid, water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:diethyl ether 49:1 to 19:1)

출처 및 근거

ORD 기록
ord-9957fb2db56244fd8e50c55f3e00daa4
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618960B2

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