Sodium hydride → Di-tert-butyl (5R)-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate

HRID 591278노트

반응식

HRID 591278 반응식
[H-].[Na+].[C:3]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Br[CH2:22][CH2:23][C@@H:24]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CN(C)C=O>[CH2:14]([O:13][C:3]([CH:4]([CH2:22][CH2:23][C@@H:24]([NH:32][C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2736712Benzyl tert-butyl malonateHCID 14193045(R)-4-Bromo-2-[[(tert-butoxy)carbonyl]amino]butanoic acid tert-butyl ester

생성물 1

HCID 117812691Di-tert-butyl (5R)-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate수율 46.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a suspension of 66 mg sodium hydride (60% in oil, 1.66 mmol) in N,N-dimethyl-formamide (10 mL) was added a solution of 456 mg benzyl tert-butyl malonate (commercial, 1.82 mmol) in N,N-dimethylformamide (5 mL) at room temperature. The mixture was stirred for one hour at room temperature before a solution of 560 mg tert-butyl (2R)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate (1.66 mmol) in N,N-dimethylformamide (5 mL) was added. The mixture was stirred for 60 hours at room temperature and was then evaporated in vacuo. The residue was purified by column chromatography on silica gel (1.5→20% ethyl acetate in hexane) to give the title compound (390 mg, 46% yield).

후처리

  1. additionwas added
  2. customwas then evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (1.5→20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-c8eacce7d299466e870aa1ce0f7d5e08
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238631B2

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