Potassium Hydroxide → HCID 25270776, compound

HRID 889729Notes

Reaction equation

HRID 889729 reaction equation
C([O:3][C:4](=[O:44])[CH:5]([C:10]1[CH:11]=[C:12]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[CH3:8][CH:7]([CH3:9])[CH2:6][CH:5]([C:10]1[CH:11]=[C:12]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][CH:35]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:32])([F:31])[F:33])=[CH:25][CH:24]=3)[CH2:17]2)[CH:15]=1)[C:4]([OH:44])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57666072HCID 57666072, compound

Product 1

HCID 25270776HCID 25270776, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To compound 47a, 4-Methyl-2-{5-[1-(4-trifluoromethoxy-benzyl)-piperidin-3-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester (67.3 mg, 0.10 mmol) in EtOH (5.2 ml) was added 2M KOH (0.52 ml, 1.04 mmol). The reaction was heated to 78° C. for 1.5 hour, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, salt exchange with 1N HCl (aqueous) gave the product as a white lyophilate, (41 mg, 63%). 1H NMR (300 MHz, MeOD) δ ppm 0.90-0.96 (m, 6 H) 1.50 (tt, J=13.38, 6.78 Hz, 1 H) 1.67 (dt, J=13.66, 6.92 Hz, 1 H) 1.88-2.03 (m, 3 H) 2.08 (d, J=17.33 Hz, 2 H) 3.03-3.14 (m, 1 H) 3.14-3.25 (m, 1 H) 3.49-3.62 (m, 2 H) 3.76 (t, J=7.72 Hz, 1 H) 4.34-4.47 (m, 2 H) 7.32 (s, 1 H) 7.42 (d, J=8.29 Hz, 2 H) 7.50 (s, 1 H) 7.57 (s, 1 H) 7.66 (d, J=8.67 Hz, 2 H) 7.78 (q, J=8.41 Hz, 4 H), Calcd for C32H33F6NO3 (M+H) 593.60, Found 594.3.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customPurification via Gilson HPLC, salt exchange with 1N HCl (aqueous)
  4. customgave the product as a white lyophilate, (41 mg, 63%)

Sources & evidence

ORD record
ord-2afde197eb944f70b8169a17f80434f8
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

Loading…