Potassium Hydroxide → HCID 25271118, compound

HRID 889736Notes

Reaction equation

HRID 889736 reaction equation
C([O:3][C:4](=[O:45])[CH:5]([C:10]1[CH:11]=[C:12]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=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][CH3:30])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:18]2[CH2:19][CH2:20][CH2:21][CH:16]([C:14]3[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:45])=[O:3])[CH:11]=[C:12]([C:35]4[CH:36]=[CH:37][C:38]([C:41]([F:42])([F:43])[F:44])=[CH:39][CH:40]=4)[CH:13]=3)[CH2:17]2)=[CH:24][C:25]=1[C:31]([F:34])([F:33])[F:32]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57666035HCID 57666035, compound

Product 1

HCID 25271118HCID 25271118, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To compound 51a, 2-{5-[1-(4-Methoxy-3-trifluoromethyl-benzyl)-piperidin-3-yl]-4′-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester (62.0 mg, 0.10 mmol) in EtOH (5.0 ml) was added 2M KOH (0.50 ml, 1.0 mmol). The reaction was heated to 78° C. for 3 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, (45.5 mg, 71%). 1H NMR (300 MHz, MeOD) δ ppm 0.95 (d, J=6.41 Hz, 6 H) 1.49 (dq, J=13.33, 6.61 Hz, 1 H) 1.67 (ddd, J=13.75, 7.16, 6.97 Hz, 1 H) 1.89-2.14 (m, 6 H) 3.00-3.14 (m, 1 H) 3.14-3.26 (m, 2 H) 3.47-3.60 (m, 2 H) 3.76 (t, J=7.72 Hz, 1 H) 3.94 (s, 3 H) 4.30-4.43 (m, 2 H) 7.27-7.34 (m, 2 H) 7.50 (s, 1 H) 7.58 (s, 1 H) 7.72-7.83 (m, 5 H) Calcd for C33H35F6NO3 (M+H) 607.63, Found 608.4.

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, (45.5 mg, 71%)

Sources & evidence

ORD record
ord-f1b019b666cf48fba1680592c8cf0b02
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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