Water → HCID 14931303、化合物

HRID 973993

反応式

HRID 973993 の反応式
[CH:1]1([C@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][N:19]([CH3:25])[CH2:20][C:21]#[C:22][CH2:23][NH2:24].O>C(Cl)(Cl)Cl>[CH3:18][N:19]([CH3:25])[CH2:20][C:21]#[C:22][CH2:23][NH:24][C:8](=[O:10])[C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 962WaterHCID 777375Cyclohexylphenylglycolic acid, (+)-HCID 12259565HCID 12259565、化合物

生成物 1

HCID 14931303HCID 14931303、化合物収率 37.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of (S)-(+)-2-cyclohexyl-2-hydroxy-2-phenylacetic acid (1.13 g, 80% ee) and N,N'-carbonyldiimidazole (0.77 g) in chloroform (5 ml) was stirred at room temperature for 2 hours. After an addition of 4-dimethylamino-2-butynylamine (0.54 g), the mixture was stirred at the same temperature for an additional hour, then the mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water and the organic layer was extracted with 1N-hydrochloric acid. The acidic solution was adjusted to pH 13 with aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with sodium chloride aqueous solution, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent to give (-)-N-(4-dimethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.60 g, 88% ee).

後処理

  1. stirringthe mixture was stirred at the same temperature for an additional hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. extractionthe organic layer was extracted with 1N-hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent

出典と根拠

ORDレコード
ord-a0ed4e33b64f471db91fd85425548675
出典データセット
uspto-grants-1991_11
特許番号
US05066680

関連ノート

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