Toluene → HCID 25269436, compound

HRID 888651Notes

Reaction equation

HRID 888651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH:25]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:26]([OH:28])=[O:27])[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[CH:14]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].C1(C)C=CC=CC=1.[C:45](Cl)(=[O:50])[CH2:46][CH:47]([CH3:49])[CH3:48]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:45](=[O:50])[CH2:46][CH:47]([CH3:49])[CH3:48])[C:9]2[CH:10]=[C:11]([CH:25]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:26]([OH:28])=[O:27])[CH:12]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=3)[CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 66054Isovaleryl chlorideHCID 517045Sodium AcetateHCID 57754989HCID 57754989, compound

Product 1

HCID 25269436HCID 25269436, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-[5-(4-chloro-phenylamino)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid (51.1 mg, 0.11 mmol), sodium acetate 40 mg, 1.1 mmol) and toluene (0.5 mL) was added isovaleryl chloride (60 μL, 0.55 mmol) and the resulting mixture was stirred at RT for 48 hr. The mixture was treated with water (10 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were dried with MgSO4, filtered and the solvent was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (gradient 0% to 30% EtOAc/heptane) to afford 16.3 mg (27%) of the title compound as a solid. 1H-NMR (CDCl3; 300 MHz): δ 7.6-7.7 (m, 4H), 6.98-7.45 (m, 7H), 3.7 (m, 1H), 2.2 (m, 2H), 2.0 (m, 1H), 1.7 (m, 1H), 1.5 (m, 1H), 1.25 (bs, 1H), 0.85-1.0 (m, 12H). Mass spectrum (ESI, m/z): Calcd. for C30H31ClF3NO3, 546.03 (M+H), found 548.26, 546.29.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationthe solvent was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (gradient 0% to 30% EtOAc/heptane)

Sources & evidence

ORD record
ord-7bd18ab00d4147b0b5bdd214f0ddb167
Source dataset
uspto-grants-2012_08
Patent number
US08247610B2

Reaction notes

Loading…