Trifluoroacetic acid → 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 494068ノート

反応式

HRID 494068 の反応式
FC(F)(F)C(O)=O.[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:38]([O:40]C(C)(C)C)=[O:39])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:24]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>ClC(Cl)C>[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:38]([OH:40])=[O:39])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:24]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 5983755810-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

生成物 1

HCID 5755909813-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid収率 94%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Trifluoroacetic acid (30 mL) was added dropwise to a stirring slurry of 10-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (10 g, 20 mmol) in dichloroethane (30 mL) under N2. The clear dark green solution was stirred at rt for 2.5 h, concentrated to dryness and stirred with EtOAc (100 mL) overnight. The solids were collected by filtration, washed with EtOAc and Et2O to yield 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (8.35 g, 18.8 mmol, 94%) was as a yellow solid which was used without further purification. 1HNMR (300 MHz, CDCl3) δ 1.13-2.16 (m, 10H), 2.74-2.88 (m, 1H), 3.84 (s, 3H), 3.89 (s, 3H), 4.06-4.29 (m, 1H), 5.54-5.76 (m, 1H), 6.98 (d, J=2.6 Hz, 1H), 7.08 (dd, J=8.4, 2.6 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.78 (dd, J=8.8, 1.1 Hz, 1H), 7.80 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 8.34 (d, J=1.1 Hz, 1H). LCMS: m/e 446 (M+H)+, ret time 3.21 min, column B, 4 minute gradient.

後処理

  1. concentrationconcentrated to dryness
  2. stirringstirred with EtOAc (100 mL) overnight
  3. filtrationThe solids were collected by filtration
  4. washwashed with EtOAc and Et2O

出典と根拠

ORDレコード
ord-b7a90577f5dd4c399d117fa803f04a75
出典データセット
uspto-grants-2009_05
特許番号
US07538102B2

反応ノート

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