Water → diethyl 1-[3-[(tert-butoxycarbonyl)amino]butan-2-yl]-1H-indole-2,6-dicarboxylate

HRID 1748257ノート

反応式

HRID 1748257 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:22][CH:23]1[CH:27]([CH3:28])OS(=O)(=O)[N:24]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].O>CN(C=O)C.CCOC(C)=O>[C:34]([O:33][C:31]([NH:24][CH:23]([CH3:22])[CH:27]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:28])=[O:32])([CH3:37])([CH3:36])[CH3:35]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2 回HCID 86682386Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

生成物 1

HCID 67236196diethyl 1-[3-[(tert-butoxycarbonyl)amino]butan-2-yl]-1H-indole-2,6-dicarboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred suspension of 60% NaH dispersion in mineral oil (596 mg, 14.9 mmol) in DMF (14 mL) at 0° C. is added a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 3.9 g, 14.9 mmol) in DMF (14 mL). The mixture is stirred for 40 min, then a solution of tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (3.8 g, 14.9 mmol) in DMF (7 mL) is added. The reaction mixture is stirred for 30 min at 0° C. and then is warmed to room temperature and stirred for 65 h. Water is added and the mixture is stirred for 15 min before EtOAc (50 mL) is added. Then the organic layer is separated, washed with aqueous NH4Cl solution, water, and brine, dried (MgSO4) and concentrated to afford the crude title compound, which was used directly in the next reaction.

後処理

  1. stirringThe reaction mixture is stirred for 30 min at 0° C.
  2. stirringstirred for 65 h
  3. additionis added
  4. customThen the organic layer is separated
  5. washwashed with aqueous NH4Cl solution, water, and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-513ca76f89ec4799a9e8582d3e5e7995
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

読み込み中…