Indoline → Tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

HRID 1167808ノート

反応式

HRID 1167808 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]([CH3:39])[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:26][CH:25]=2)=[O:22])=[CH:16][C:15]=1[O:40][CH3:41].[NH:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1>ClCCl.C(N(CC)CC)C>[N:42]1([C:5]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH:30]([CH3:39])[CH2:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])=[CH:26][CH:25]=3)=[O:22])=[CH:16][C:15]=2[O:40][CH3:41])=[O:11])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1

参加物

6

反応物 3

HCID 10328IndolineHCID 94429TriphosgeneHCID 22994176Tert-butyl 3-[4-({4-amino-3-methoxyphenyl}acetylamino)phenyl]butyrate

生成物 1

HCID 22994266Tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

Triphosgene (150 mg) was added to a stirred solution of tert-butyl 3-[4-({4-amino-3-methoxyphenyl}acetylamino)phenyl]butyrate (540 mg, Reference Example 2) in dichloromethane (50 ml) at 0-5° C. under an atmosphere of nitrogen. After stirring for one hour the mixture was treated with a solution of indoline (0.15 ml) in dichloromethane (2.5 ml) and triethylamine (0.51 ml). This mixture was allowed to stand at room temperature overnight and then evaporated. The residual gummy solid was suspended in water and the suspension was acidified to pH 1 by addition of hydrochloric acid. The resulting pale green solid was filtered and then subjected to flash chromatography on silica eluting with 0.2% to 1% methanol in dichloromethane to give the title compound (580 mg) as an off-white solid.

後処理

  1. waitto stand at room temperature overnight
  2. customevaporated
  3. additionthe suspension was acidified to pH 1 by addition of hydrochloric acid
  4. filtrationThe resulting pale green solid was filtered

出典と根拠

ORDレコード
ord-4b586571773d4d0d8afe78a917fb1476
出典データセット
uspto-grants-2003_09
特許番号
US06620832B2

反応ノート

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