Benzene → 4-Oxo-4-phenyl-2-[(trifluoroacetyl)amino]butanoic acid

HRID 1725617Notes

Reaction equation

HRID 1725617 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][CH:6]1[C:11](=[O:12])[O:10][C:8](=[O:9])[CH2:7]1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[O:9]=[C:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:7][CH:6]([NH:5][C:3](=[O:4])[C:2]([F:14])([F:13])[F:1])[C:11]([OH:10])=[O:12]

Participants

4

Reactant 3

HCID 241BenzeneHCID 3128053-[(Trifluoroacetyl)amino]succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5696304-Oxo-4-phenyl-2-[(trifluoroacetyl)amino]butanoic acid

Procedure

A solution of 3-[(trifluoroacetyl)amino]succinic anhydride (4.00 g, 19.0 mmol) and aluminum chloride (5.56 g, 41.7 mmol) in benzene (80 mL) was refluxed for 5 h, then cooled in an ice bath and quenched by the slow addition of water. The reaction mixture was worked up with ethyl acetate and 10% hydrochloric acid. The residue was purified by chromatography (silica gel, 100% methylene chloride to 90/10/1/1 methylene chloride/methanol/acetic acid/water gradient elution). Recrystallization of the resulting oil from methylene chloride/hexanes produced the title compound as a white solid (3.00 g). 1H NMR (500 MHz, (d6-acetone) □ 11.56 (bs, 1H), 8.63 (bs, 1H), 8.06 (dd, J=8.3, 1.2 Hz, 2H), 7.70-7.67 (m, 1H), 7.57 (t, J=7.7 Hz, 2H), 5.14-5.10 (m, 1H), 3.84 (dd, J=18.3, 6.8 Hz, 1H), 3.77 (dd, J=18.1, 4.6 Hz, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. customquenched by the slow addition of water
  3. customThe residue was purified by chromatography (silica gel, 100% methylene chloride to 90/10/1/1 methylene chloride/methanol/acetic acid/water gradient elution)
  4. customRecrystallization of the resulting oil from methylene chloride/hexanes

Sources & evidence

ORD record
ord-9c331cb77223402aa2c088a6cfa95c7f
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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