Potassium Hydroxide → HCID 25271447, compound

HRID 889740Notes

Reaction equation

HRID 889740 reaction equation
C([O:3][C:4](=[O:47])[CH:5]([C:10]1[CH:11]=[C:12]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[F:32][C:29]([F:30])([F:31])[C:27]1[CH:28]=[C:23]([CH:24]=[C:25]([C:33]([F:34])([F:36])[F:35])[CH:26]=1)[CH2:22][N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:14]2[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:47])=[O:3])[CH:11]=[C:12]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:44])[F:45])=[CH:39][CH:38]=3)[CH:13]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57665949HCID 57665949, compound

Product 1

HCID 25271447HCID 25271447, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To compound 53a, 2-{5-[1-(3,5-Bis-trifluoromethyl-benzyl)-piperidin-3-yl]-4′-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester (106.5 mg, 0.16 mmol) in EtOH (7.9 ml) was added 2M KOH (0.79 ml, 1.6 mmol). The reaction was heated to 78° C. for 1 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, (72.3 mg, 67%). 1H NMR (300 MHz, MeOD) δ ppm 0.94 (dd, J=6.22, 2.07 Hz, 6 H) 1.50 (dt, J=13.47, 6.64 Hz, 1 H) 1.67 (ddd, J=13.75, 7.16, 6.97 Hz, 1 H) 1.89-2.04 (m, 3 H) 2.06-2.14 (m, 2 H) 3.11-3.19 (m, 2 H) 3.33-3.43 (m, 1H) 3.51-3.56 (m, 1 H) 3.61-3.65 (m, 1 H) 3.77 (t, J=7.72 Hz, 1 H) 4.49-4.64 (m, 2 H) 7.34 (s, 1 H) 7.55 (d, J=18.09 Hz, 2 H) 7.78 (q, J=8.54 Hz, 4 H) 8.16 (s, 1 H) 8.25 (s, 2 H) Calcd for C33H32F9NO2 (M+H) 645.60, Found 646.3.

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, (72.3 mg, 67%)

Sources & evidence

ORD record
ord-c7a5bbbbc7324a55a327b3a9c1cdc0e0
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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