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

HRID 1173774ノート

反応式

HRID 1173774 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-039f8cf280294c74b2105a52a4431312
出典データセット
uspto-grants-2010_11
特許番号
US07834190B2

反応ノート

読み込み中…