Sodium hydride → [(2-Benzyloxy-4-chlorophenyl)-tert-butoxycarbonylamino]-acetic Acid Methyl Ester

HRID 660823

反応式

HRID 660823 の反応式
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C=O)C>[CH3:31][O:30][C:28](=[O:29])[CH2:27][N:7]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:23]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 220109632-benzyloxy-4-chloro-N-tert-butoxycarbonylaniline

生成物 1

HCID 68838982[(2-Benzyloxy-4-chlorophenyl)-tert-butoxycarbonylamino]-acetic Acid Methyl Ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2-benzyloxy-4-chlorophenyl)-carbamic acid tert-butyl ester (14.75 g, 44.2 mmol) in DMF (150 mL) at 0° C. is added NaH (1.94 g, 60% in mineral oil, 48.6 mmol) and the mixture is stirred at 0° C. for 10 min. To this is added methyl bromoacetate (5.04 mL, 53 mmol) and the mixture is stirred at RT for 8 h. The mixture is poured into ice/water (150 mL) and is extracted with EtOAc (700 mL). The organic phase is washed with 1N HCl (3×150 mL) and brine (150 mL) then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 5-10% EtOAc/hexane as eluent to give the title compound.

後処理

  1. stirringthe mixture is stirred at RT for 8 h
  2. extractionis extracted with EtOAc (700 mL)
  3. washThe organic phase is washed with 1N HCl (3×150 mL) and brine (150 mL)
  4. dry with materialthen is dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by flash chromatography

出典と根拠

ORDレコード
ord-341a173e958040c1b86804bbf24b6716
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

関連ノート

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