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

HRID 591278ノート

反応式

HRID 591278 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c8eacce7d299466e870aa1ce0f7d5e08
出典データセット
uspto-grants-2016_01
特許番号
US09238631B2

反応ノート

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