Valproic Acid → HCID 11841479, compound
Reaction equation
CCN(CC)CC.[CH2:8]([CH:11]([CH2:15][CH2:16][CH3:17])[C:12]([OH:14])=O)[CH2:9][CH3:10].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:42][C:43]1[CH:44]=[C:45]([CH:47]=[CH:48][CH:49]=1)[NH2:46]>CN(C=O)C.O>[Br:42][C:43]1[CH:44]=[C:45]([NH:46][C:12](=[O:14])[CH:11]([CH2:8][CH2:9][CH3:10])[CH2:15][CH2:16][CH3:17])[CH:47]=[CH:48][CH:49]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Et3N (3.24 mL, 23.25 mmol) was added to a solution of 2-propylpentanoic acid in (2 g, 11.62 mmol) in DMF. The reaction mixture was cooled to 0° C. HATU (6.63 g, 17.4 mmol) was added to the reaction mixture which was stirred for 15 min and then 3-bromoaniline (2.5 g, 17.43 mmol) was added. The reaction mixture was stirred for 2 h at 0° C. The reaction mixture was diluted with H2O, extracted with EtOAc, and organic layer was concentrated under reduced pressure. The residue was washed with pentane to give N-(3-bromophenyl)-2-propylpentanamide as a white solid. Yield (1.6 g, 47%); 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.23 (d, J=7.6 Hz, 1H), 7.17 (t, J=8.0 Hz, 1H), 7.12 (bs, 1H), 2.21-2.14 (m, 1H), 1.73-1.63 (m, 2H), 1.51-1.45 (m, 2H), 1.43-1.25 (m, 4H), 0.92 (t, J=7.2 Hz, 6H).
Workup
- stirringThe reaction mixture was stirred for 2 h at 0° C
- extractionextracted with EtOAc, and organic layer
- concentrationwas concentrated under reduced pressure
- washThe residue was washed with pentane
Sources & evidence
- ORD record
- ord-0a032929b0024dbab58e284278cbe333
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674137B2
Reaction notes
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