Dimethylformamide → N-methoxycarbonyl-O-methyl-L-tyrosine benzyl ester

HRID 274088ノート

反応式

HRID 274088 の反応式
[CH2:1]([O:8][C:9](=[O:24])[C@H:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:11][C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+].CN(C)C=O>ClCCl>[CH2:1]([O:8][C:9](=[O:24])[C@H:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:27])=[CH:19][CH:18]=1)[NH:11][C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54118506N-methoxycarbonyl-L-tyrosine benzyl ester

生成物 1

HCID 54335584N-methoxycarbonyl-O-methyl-L-tyrosine benzyl ester収率 69.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of N-methoxycarbonyl-L-tyrosine benzyl ester (22.0 g), methyl iodide (10.8 ml), potassium carbonate (24.0 g), and N,N-dimethylformamide (87 ml) was stirred at ambient temperature for 5 hours. The mixture was diluted with dichloromethane (87 ml) and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was purified by pulverization with petroleum ether to give N-methoxycarbonyl-O-methyl-L-tyrosine benzyl ester (16.0 g).

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by pulverization with petroleum ether

出典と根拠

ORDレコード
ord-4dc3430c805b41c6a7b5b510da9aceff
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

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