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

反応式

HRID 31051 の反応式
[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]

参加物

6

反応物 2

HCID 5207692-(Trifluoromethyl)oxirane2 回HCID 58972520((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester

生成物 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 ester収率 76%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

((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+).

後処理

  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

出典と根拠

ORDレコード
ord-fd4c0dd8cdad42c99f8b14c94dda3323
出典データセット
uspto-grants-2008_09
特許番号
US07425551B2

関連ノート

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