Trifluoroacetic acid → Trifluoroacetic acid

HRID 1354508노트

반응식

HRID 1354508 반응식
Br[CH2:2][C:3]([C:5]1[N:6]([CH2:24][C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[C:7]2[C:12]([C:13]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:11][CH:10]=[C:9]([C:20]([O:22]C)=[O:21])[CH:8]=2)=O.[C:33]([NH:37][C:38]([NH2:40])=[S:39])([CH3:36])([CH3:35])[CH3:34].[OH-].[Na+].[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>CS(C)=O>[C:33]([NH:37][C:38]1[S:39][CH:2]=[C:3]([C:5]2[N:6]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:26])[C:7]3[C:12]([C:13]=2[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:11][CH:10]=[C:9]([C:20]([OH:22])=[O:21])[CH:8]=3)[N:40]=1)([CH3:36])([CH3:35])[CH3:34].[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium Hydroxide2회HCID 737374N-(tert-Butyl)thioureaHCID 21105283Methyl 2-(2-bromo-ethanoyl)-3-cyclohexyl-1-(2-morpholin-4yl-2-oxo-ethyl)-1H-indole-6carboxylate

생성물 2

HCID 6422Trifluoroacetic acidHCID 211052522-(2-Tert-butylamino-thiazol-4-yl)-3-cyclohexyl-1-(2-morpholin-4-yl-2-oxo-ethyl)-1h-indole-6-carboxylic acid

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

The bromomethylketone of example 11 (39.6 mg, 0.078 mmol, 1 equiv.) was dissolved in DMSO (1 mL) and N-tertbutylthiourea (12.4 mg, 0.094 mmol, 1.2 equiv.) was added. The mixture was stirred for 2 h at room temperature. 10 N NaOH (24 μL) was added and after stirring for 4 h at room temperature, another portion of 10 N NaOH (24 μL) was added and the mixture stirred 24 h at room temperature to complete the hydrolysis. The reaction mixture was then neutralized by addition of TFA and the title product of example 12 isolated directly from the reaction mixture by preparative HPLC as a white amorphous TFA salt (21 mg).

후처리

  1. stirringafter stirring for 4 h at room temperature
  2. stirringthe mixture stirred 24 h at room temperature
  3. customthe hydrolysis

출처 및 근거

ORD 기록
ord-ae2cc7eff3af45ef847ef2e5bd812cbb
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223785B2

반응 노트

불러오는 중…