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

HRID 1748248노트

반응식

HRID 1748248 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][C@@H:23]1OS(=O)(=O)[N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]1>CN(C=O)C>[C:33]([O:32][C:30]([NH:25][CH2:24][C@H: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:31])([CH3:36])([CH3:35])[CH3:34]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2회

생성물 1

HCID 67235704diethyl 1-{(2R)-1-[(tert-butoxycarbonyl)amino]propan-2-yl}-1H-indole-2,6-dicarboxylate수율 76.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A stirred suspension of 60% NaH (371 mg, 9.3 mmol) in DMF (10 mL) is cooled in an ice bath, and a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 2.6 g, 10.1 mmol) in DMF (10 mL) is added. The mixture is stirred for 20 min, then a solution of tert-butyl (5S)-5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (2.0 g, 8.4 mmol) in DMF (10 mL) is added. The reaction mixture is stirred for 30 min at 0° C. and then warmed to room temperature and stirred for 48 h. The reaction is poured into ice water and the resultant solid is removed by filtration. The filtrate is acidified to pH 3 with 1N aqueous HCl and extracted with EtOAc. The combined extracts are washed with water, brine, dried (Na2SO4) and concentrated to afford the title compound (2.7 g, crude) as an oil.

후처리

  1. temperatureis cooled in an ice bath
  2. stirringThe reaction mixture is stirred for 30 min at 0° C.
  3. stirringstirred for 48 h
  4. customthe resultant solid is removed by filtration
  5. extractionextracted with EtOAc
  6. washThe combined extracts are washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6b99260e1a564e6199bf773a227fc2bf
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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