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

HRID 274088노트

반응식

HRID 274088 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4dc3430c805b41c6a7b5b510da9aceff
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387710

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