Dichloromethane → (1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine

HRID 16330

반응식

HRID 16330 반응식
FC(F)(F)C(O)=O.C(Cl)Cl.C(OC(=O)[NH:17][C@H:18]([C:39]1[CH:44]=[C:43]([F:45])[C:42]([F:46])=[C:41]([F:47])[CH:40]=1)[C@H:19]([O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:20])(C)(C)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Si:22]([O:21][C@H:19]([CH3:20])[C@H:18]([NH2:17])[C:39]1[CH:44]=[C:43]([F:45])[C:42]([F:46])=[C:41]([F:47])[CH:40]=1)([C:35]([CH3:36])([CH3:37])[CH3:38])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68718850tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

생성물 1

HCID 68719033(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine수율 91.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Trifluoroacetic acid (0.5 mL) was added to a methylene chloride solution (2 mL) of [(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester (370 mg). This reaction solution was stirred at room temperature for 11 hr. To this reaction solution, a saturated sodium hydrogencarbonate aqueous solution and ethyl acetate were added. The organic layer was separated, washed with a saturated sodium hydrogencarbonate aqueous solution and then with saturated saline. Then, the organic layer was concentrated under reduced pressure to give 275 mg of the title compound. The physical property values of this compound were as follows:

후처리

  1. customThe organic layer was separated
  2. washwashed with a saturated sodium hydrogencarbonate aqueous solution
  3. concentrationThen, the organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e6ceb06e3c3d40b6964115651d1afece
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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