Methyl iodide → methyl(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoate

HRID 2256434Notes

Reaction equation

HRID 2256434 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C:25](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:25])=[CH:21][CH:22]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 11359854methyl(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32.94 g (100 mmol) of N-benzyloxycarbonyl-tyrosine methyl ester is mixed in 200 ml of DMF with 27.64 g (200 mmol) of ground potassium carbonate. 15.6 g (110 mmol) of iodomethane is instilled in this suspension and stirred overnight at room temperature. The solution is concentrated by evaporation, distributed between ethyl acetate and water, and, after drying (Na2SO4), the organic phase is mixed with hexane. The title compound crystallizes out.

Workup

  1. concentrationThe solution is concentrated by evaporation
  2. dry with materialafter drying (Na2SO4)
  3. additionthe organic phase is mixed with hexane
  4. customThe title compound crystallizes out

Sources & evidence

ORD record
ord-0a3c35d8243a479cb154435209b0dd9d
Source dataset
uspto-grants-1997_08
Patent number
US05654467

Reaction notes

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