Trifluoroacetic acid → HCID 11599367、化合物

HRID 2222957ノート

反応式

HRID 2222957 の反応式
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@H:18]([N:31]2[C:35](=[O:36])[CH:34]([C:37]3[CH:46]=[CH:45][C:40]4[O:41][CH2:42][CH2:43][O:44][C:39]=4[CH:38]=3)[NH:33][C:32]2=[O:47])[C:19](=[O:30])[NH:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=2)=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:29][O:28][C:26]([C:24]1[N:25]=[C:21]([NH:20][C:19](=[O:30])[C@@H:18]([N:31]2[C:35](=[O:36])[CH:34]([C:37]3[CH:46]=[CH:45][C:40]4[O:41][CH2:42][CH2:43][O:44][C:39]=4[CH:38]=3)[NH:33][C:32]2=[O:47])[CH2:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][CH:9]=2)[S:22][CH:23]=1)=[O:27]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86604044HCID 86604044、化合物

生成物 1

HCID 11599367HCID 11599367、化合物収率 55.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cold solution of 3-[(S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2,5-dioxo-imidazolidin-1-yl]-2-(4-methoxycarbonyl-thiazol-2-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (78 mg, 0.118 mmol) in dichloromethane (10 mL), was added trifluoroacetic acid (2 mL, 26.0 mmol). The reaction mixture was stirred at room temperature for 1 hour. The volatiles were removed in vacuo and the residue was dissolved in ethyl acetate (100 mL), washed once with cold saturated aqeous sodium bicarbonate, water, brine and dried over sodium sulfate. The solvent was removed and the residue was purified by chromatographed over silica gel gradient eluted between 50% and 75% ethyl acetate in hexanes to afford 2-[(S)-2-[4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2,5-dioxo-imidazolidin-1-yl]-3-(1H-indol-3-yl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (37 mg, 55%).

後処理

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed once with cold saturated aqeous sodium bicarbonate, water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified
  7. customby chromatographed over silica gel gradient
  8. washeluted between 50% and 75% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-c5d2ee4b569e439c8b5a2411f8d5c587
出典データセット
uspto-grants-2008_05
特許番号
US07371869B2

反応ノート

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