Water → O-benzyl-N-trifluoroacetyltyrosine

HRID 1490014Notes

Reaction equation

HRID 1490014 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C[O:29][C:30](=O)[C:31]([F:34])([F:33])[F:32].O>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH:15][C:30](=[O:29])[C:31]([F:34])([F:33])[F:32])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9893Methyl trifluoroacetateHCID 725701O-benzyl-L-tyrosine

Product 1

HCID 53698430O-benzyl-N-trifluoroacetyltyrosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

112.5 g (0.41 mmol) of O-benzyltyrosine is suspended in 1 liter of dry methanol and mixed at room temperature with 58.9 ml (0.42 mol) of triethylamine. After addition of 67 ml (0.53 mol) of trifluoroacetic acid methyl ester, it is stirred for 130 hours at room temperature with exclusion of water. The unreacted initial material is separated and the leaving components are removed by shaking with ethyl acetate/aqueous hydrochloric acid. The ethyl acetate phase is decolored with activated carbon. After evaporation of the solvent, 120.7 g (80% of theory) of colorless crystals is obtained.

Workup

  1. customThe unreacted initial material is separated
  2. customthe leaving components are removed
  3. customAfter evaporation of the solvent, 120.7 g (80% of theory) of colorless crystals
  4. customis obtained

Sources & evidence

ORD record
ord-47e01353483344b7af0f28a2d5f48405
Source dataset
uspto-grants-1997_10
Patent number
US05681544

Reaction notes

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