Triethylamine → O-benzyl-N-trifluoroacetyltyrosine

HRID 374745Notes

Reaction equation

HRID 374745 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:30][C:31](=O)[C:32]([F:35])([F:34])[F:33])C>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:31](=[O:30])[C:32]([F:35])([F:34])[F:33])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl 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 combined at room temperature with 58.9 ml (0.42 mol) of triethylamine. After adding 67 ml (0.53 mol) of trifluoroacetic acid ethyl ester, the mixture is stirred at room temperature for 130 hours under exclusion of moisture. The mixture is separated from unreacted starting material and volatile components are removed by shaking with ethyl acetate/aqueous hydrochloric acid. The ethyl acetate phase is decolorized with activated carbon. Evaporation of the solvents yields 120.7 g (80% of theory) of colorless crystals. Melting point: 149°-150° C.

Workup

  1. customThe mixture is separated
  2. customare removed
  3. stirringby shaking with ethyl acetate/aqueous hydrochloric acid
  4. customEvaporation of the solvents
  5. customyields 120.7 g (80% of theory) of colorless crystals

Sources & evidence

ORD record
ord-fbd95790bc8a46c48bfb733137faeec6
Source dataset
uspto-grants-1996_01
Patent number
US05482700

Reaction notes

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