Isobutyronitrile → (4S,5S)-N-cyclopropyl-2-isopropyl-4-benzyl-4,5-dihydro-1,3-oxazole-5-carboxamide

HRID 1173774노트

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HRID 1173774 반응식
[CH:1]1([NH:4][C:5]([C@@H:7]2[C@@H:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8]2)=[O:6])[CH2:3][CH2:2]1.[C:17](#[N:21])[CH:18]([CH3:20])[CH3:19].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C@H:7]2[O:8][C:17]([CH:18]([CH3:20])[CH3:19])=[N:21][C@H:9]2[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:6])[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 6559IsobutyronitrileHCID 516892Sodium BicarbonateHCID 59203389(2S,3R)-3-benzyl-2-oxiranecarboxylic cyclopropylamide

생성물 1

HCID 59203393(4S,5S)-N-cyclopropyl-2-isopropyl-4-benzyl-4,5-dihydro-1,3-oxazole-5-carboxamide수율 96%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
5 °C

실험 절차

(2S,3R)-3-Benzyl-2-oxiranecarboxylic cyclopropylamide (50 mg) and isobutyronitrile (2 ml) were mixed, and the mixture was cooled to 5° C. Boron trifluoride diethyl ether complex (2.5 equivalents) was gradually added, and the mixture was stirred at 5 to 20° C. for 2 hours. A mixture solution of ethyl acetate (10 ml) and saturated aqueous solution of sodium hydrogencarbonate (5 ml) was kept cooled at 5° C., and the reaction mixture was gradually added thereinto dropwise. The aqueous layer was removed, and then the solvent was evaporated away under reduced pressure to obtain the title compound as a brown solid (63 mg, yield: 96%).

후처리

  1. additionBoron trifluoride diethyl ether complex (2.5 equivalents) was gradually added
  2. additionthe reaction mixture was gradually added
  3. customThe aqueous layer was removed
  4. customthe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-039f8cf280294c74b2105a52a4431312
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834190B2

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