Trifluoroacetic acid → Trifluoroacetic acid

HRID 1364968ノート

反応式

HRID 1364968 の反応式
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]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium Hydroxide2 回HCID 737374N-(tert-Butyl)thioureaHCID 21105283Methyl 2-(2-bromo-ethanoyl)-3-cyclohexyl-1-(2-morpholin-4yl-2-oxo-ethyl)-1H-indole-6carboxylate

生成物 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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9927000c0d364b42b1a3ff6f8941cd86
出典データセット
uspto-grants-2011_02
特許番号
US07888363B2

反応ノート

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