Trifluoroacetic acid → (S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol

HRID 885204노트

반응식

HRID 885204 반응식
FC(F)(F)C(O)=O.C(OC([N:15]1[C@@H:19]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH2:18][O:17]C1(C)C)=O)(C)(C)C.[OH-].[Na+]>O.C(#N)C.C(OCC)(=O)C>[NH2:15][C@@H:19]([CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][N:24]=1)[CH2:18][OH:17]

참가 물질

7

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59173205(S)-2,2-dimethyl-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-oxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 59173196(S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol수율 113.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of trifluoroacetic acid (0.23 ml) in water (9 ml) was added dropwise a solution of (S)-2,2-dimethyl-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-oxazolidine-3-carboxylic acid tert-butyl ester (390 mg) in acetonitrile (1.5 ml). The mixture was heated for 90 min at 80° C. with stirring. The mixture was then cooled to room temperature and made basic by addition of 2 M aq. sodium hydroxide solution, then diluted with ethyl acetate and washed sequentially with water and with saturated brine. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to give (S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol (284 mg, quant.) as a yellow oil. MS (ISP): 251.2 ([M+H]+).

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. washwashed sequentially with water and with saturated brine
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9b14865f1dae48ec9b0b379f9491f085
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242153B2

반응 노트

불러오는 중…