2-(Trifluoromethyl)oxirane → [(S)-5-(3,3,3-Trifluoro-2-hydroxy-propyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-carbamic acid tert-butyl ester

HRID 31051

반응식

HRID 31051 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]1=2)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]([F:31])([F:30])[CH:27]1[O:29][CH2:28]1>CN(C=O)C.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:28][CH:27]([OH:29])[C:26]([F:31])([F:30])[F:25])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]1=2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 2

HCID 5207692-(Trifluoromethyl)oxirane2회HCID 58972520((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 58972484[(S)-5-(3,3,3-Trifluoro-2-hydroxy-propyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-carbamic acid tert-butyl ester수율 76%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester (108 mg, 0.33 mmol) and 1,1,1-trifluoro-2,3-epoxypropane (762 mg, 6.7 mmol) were dissolved in DMF (2 ml) and heated to 90° C. for 4 h in a sealed tube. After addition of another 500 mg of 1,1,1-trifluoro-2,3-epoxypropane, heating was continued for 18 h. The mixture was diluted with ethyl acetate and water (10 ml each), separated and the aqueous phase extracted twice with each 10 ml ethyl acetate. The combine organic phases are dried over magnesium sulfate and evaporated to dryness. Chromatography (silica, eluent heptanes/ethyl acetate gradient from 1 to 30%) afforded the title compound as white solid (76%). MS: m/e=437(M+H+).

후처리

  1. temperatureheating
  2. customseparated
  3. extractionthe aqueous phase extracted twice with each 10 ml ethyl acetate
  4. dry with materialThe combine organic phases are dried over magnesium sulfate
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-fd4c0dd8cdad42c99f8b14c94dda3323
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425551B2

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