Sodium hydride → diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate

HRID 1748269노트

반응식

HRID 1748269 반응식
[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]1OS(=O)(=O)[N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][CH2:24]1.[NH4+].[Cl-]>CN(C=O)C>[C:34]([O:33][C:31]([NH:26][CH2:25][CH2:24][CH:23]([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])[CH3:22])=[O:32])([CH3:37])([CH3:36])[CH3:35]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2회HCID 86682388Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide

생성물 1

HCID 67236468diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate수율 133.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
0 °C

실험 절차

To a stirred suspension of 60% NaH dispersion in mineral oil (78.8 mg, 2.0 mmol) in DMF (2.5 mL) cooled to 0° C. is added a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 561 mg, 2.1 mmol) in DMF (3 mL). The mixture is stirred for 20 min and a solution of tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide (450 mg, 1.8 mmol) in DMF (2.5 mL) is added. The reaction mixture is stirred for 30 min at 0° C. and it is warmed to room temperature and stirred for 48 h. Saturated NH4Cl solution is added and the reaction mixture is extracted with EtOAc. The organic layer is separated, washed with water, then brine, dried (MgSO4) and concentrated to afford the title compound (1.04 g, 50% pure) as an oil.

후처리

  1. stirringThe reaction mixture is stirred for 30 min at 0° C.
  2. temperatureit is warmed to room temperature
  3. stirringstirred for 48 h
  4. extractionthe reaction mixture is extracted with EtOAc
  5. customThe organic layer is separated
  6. washwashed with water
  7. dry with materialbrine, dried (MgSO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c12f7bfa7754c81b77bf51e26af72f3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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