Acetic Acid → HCID 86616774, compound

HRID 1725619Notes

Reaction equation

HRID 1725619 reaction equation
[CH2:1]([NH:5][C:6](=[O:24])[CH:7]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:2]([CH3:4])[CH3:3].C(O)(=O)C>C1(C)C=CC=CC=1>[F:20][C:19]([F:22])([F:21])[C:18]([NH:17][C:7]1[C:6](=[O:24])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=1)=[O:23]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86616773HCID 86616773, compound

Product 1

HCID 86616774HCID 86616774, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-isobutyl-4-oxo-4-phenyl-2-[(trifluoroacetyl)amino]butanamide (0.500 g, 1.45 mmol) and acetic acid (0.831 mL, 14.5 mmol) in toluene (15 mL) was heated to reflux. After 48 hours the reaction was cooled and concentrated. The crude product was purified by chromatography (silica gel, 0 to 50% ethyl acetate in hexane gradient elution) to give the title compound as a solid (0.412 g). MS 327 (M+1) 1H NMR (500 MHz, CDCl3) □ 7.40-7.36 (m, 3H), 7.20 (d, J=2.0 Hz, 1H), 7.12-7.11 (m, 2H), 5.12 (d, J=2.0 Hz, 1H), 3.53 (dd, J=13.9, 9.4 Hz, 1H), 2.61 (dd, J=13.9, 5.9 Hz, 1H), 1.89-1.80 (m, 1H), 0.87 (d, J=6.6 Hz, 3H), 0.84 (d, J=6.6 Hz, 3H).

Workup

  1. temperatureAfter 48 hours the reaction was cooled
  2. concentrationconcentrated
  3. customThe crude product was purified by chromatography (silica gel, 0 to 50% ethyl acetate in hexane gradient elution)

Sources & evidence

ORD record
ord-ebc8ffde3d65418a9c8b2de0514b8c7e
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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