Potassium Hydroxide → HCID 25271117, compound

HRID 889734Notes

Reaction equation

HRID 889734 reaction equation
C([O:3][C:4](=[O:43])[CH:5]([C:10]1[CH:11]=[C:12]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:32]=[CH:31][C:26]4[N:27]=[N:28][N:29]([CH3:30])[C:25]=4[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:33]2[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:37][CH:38]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:32]=[CH:31][C:26]4[N:27]=[N:28][N:29]([CH3:30])[C:25]=4[CH:24]=3)[CH2:17]2)[CH:15]=1)[C:4]([OH:43])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57665977HCID 57665977, compound

Product 1

HCID 25271117HCID 25271117, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To compound 50a, 4-Methyl-2-{5-[1-(3-methyl-3H-benzotriazol-5-ylmethyl)-piperidin-3-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester (59.0 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 2 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, (32 mg, 53%). 1H NMR (400 MHz, MeOD) δ ppm 0.89-0.97 (m, 6 H) 1.49 (dt, J=13.39, 6.63 Hz, 1 H) 1.62-1.70 (m, J=13.72, 7.09, 6.94, 2.32 Hz, 1 H) 1.90-2.02 (m, 3 H) 2.11 (s, 2 H) 3.11-3.20 (m, 2 H) 3.30-3.50 (m, 1H) 3.57 (s, 2 H) 4.75 (t, J=7.70 Hz, 1 H) 4.33-4.37 (m, 3 H) 4.53-4.62 (m, 2 H) 7.32 (s, 1 H) 7.50 (s, 1 H) 7.56 (s, 1 H) 7.72-7.81 (m, 5 H) 7.90 (d, J=8.56 Hz, 1 H) 8.23 (s, 1 H) Calcd for C32H35F3NO4 (M+H) 564.64, Found 565.3.

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, (32 mg, 53%)

Sources & evidence

ORD record
ord-d5d8cbfb1f5143fd80bca646ecd3bbdd
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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