Hydrochloric Acid → N-Trifluoroacetyl 4-benzoylphenylalanine

HRID 11906

Reaction equation

HRID 11906 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3](OC)=[O:4].C(N(CC)CC)C.[C:16]([C:24]1[CH:35]=[CH:34][C:27]([CH2:28][C@@H:29]([C:31]([OH:33])=[O:32])[NH2:30])=[CH:26][CH:25]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CO.C(OCC)(=O)C>[F:8][C:2]([F:1])([F:7])[C:3]([NH:30][C@H:29]([C:31]([OH:33])=[O:32])[CH2:28][C:27]1[CH:26]=[CH:25][C:24]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:35][CH:34]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9893Methyl trifluoroacetateHCID 7020128p-benzoyl-L-phenylalanine

Product 1

HCID 86605421N-Trifluoroacetyl 4-benzoylphenylalanineYield 18.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl trifluoroacetate (89.6 μL, 891 μmoles) and triethylamine (104 μL, 743 μmoles) were added to a suspension of 4-benzoylphenylalanine (200 mg, 743 μmoles) in methanol (0.5 mL). The reaction was stirred vigorously for 24 h and then acidified with 1 N HCl until a pH of 2 was obtained. The mixture was added to ethyl acetate (10 mL), washed with 1 N HCl (2×10 mL), dried over MgSO4, and concentrated in vacuo to yield a white solid (49.7 mg, 136 μmoles, 18%). LRMS: not performed. 1H NMR: spectrum is consistent with the predicted structure.

Workup

  1. customwas obtained
  2. washwashed with 1 N HCl (2×10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95720159bc9c4e74bfd87770a2679b41
Source dataset
uspto-grants-2006_08
Patent number
US07098196B1

Linked notes

Loading…