Water → HCID 14931303, 화합물

HRID 973993

반응식

HRID 973993 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 777375Cyclohexylphenylglycolic acid, (+)-HCID 12259565HCID 12259565, 화합물

생성물 1

HCID 14931303HCID 14931303, 화합물수율 37.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a0ed4e33b64f471db91fd85425548675
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05066680

연결된 노트

불러오는 중…