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

HRID 274088Notes

Reaction equation

HRID 274088 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4dc3430c805b41c6a7b5b510da9aceff
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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