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

HRID 16357

반응식

HRID 16357 반응식
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[C:24]([O:28][C:29](=[O:44])[NH:30][C@H:31]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C@H:32]([OH:34])[CH3:33])([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>O.C(OCC)(=O)C>[C:24]([O:28][C:29](=[O:44])[NH:30][C@H:31]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C@H:32]([O:34][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:33])([CH3:25])([CH3:26])[CH3:27]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 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 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

In nitrogen atmosphere, tert-butyldiphenylsilyl chloride (2.0 mL) was added dividedly four times to a DMF solution (3 mL) of [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)-propyl]carbamic acid tert-butyl ester (610 mg) and imidazole (817 mg). The resulting reaction solution was stirred at room temperature for 3 hr, and ethyl acetate and water were added thereto. The organic layer was separated and washed with 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. Then, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:diethyleter=49:1 to 19:1) to give 684 mg of the title compound. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. customThe organic layer was separated
  3. washwashed with 1 N hydrochloric acid, water
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:diethyleter=49:1 to 19:1)

출처 및 근거

ORD 기록
ord-33dcc2959eb240baaf16901c524efb4b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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