Sodium Hydroxide → HCID 118307874, compound

HRID 718459Notes

Reaction equation

HRID 718459 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:41])=[N:14][C:15]([CH3:40])=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[CH:28][CH:27]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:41])=[N:14][C:15]([CH3:40])=[C:16]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=3)=[CH:30][CH:31]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118314216HCID 118314216, compound

Product 1

HCID 118307874HCID 118307874, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-(pyridin-4-ylmethoxy)phenyl)pyridin-3-yl)acetate (0.013 g, 0.023 mmol) and 1M NaOH (0.232 ml, 0.232 mmol) in EtOH (1 mL) was refluxed for 6 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-(pyridin-4-ylmethoxy)phenyl)pyridin-3-yl)acetic acid (0.0101 g, 0.019 mmol, 82% yield) as solid. 1H NMR (500 MHz, DMSO-d6) δ 8.58 (d, J=5.5 Hz, 2H), 7.45 (d, J=5.1 Hz, 2H), 7.25 (d, J=7.7 Hz, 1H), 7.14-7.05 (m, 3H), 5.86 (s, 1H), 5.32-5.23 (m, 2H), 3.22 (d, J=12.1 Hz, 1H), 2.78 (t, J=12.3 Hz, 1H), 2.44 (s, 3H), 2.17 (d, J=11.4 Hz, 1H), 2.06 (s, 3H), 1.95-1.86 (m, 1H), 1.53-1.44 (m, 1H), 1.33-1.23 (m, 1H), 1.19-1.14 (m, 1H), 1.13 (s, 9H), 1.00 (d, J=12.5 Hz, 1H), 0.85 (s, 3H), 0.56 (s, 3H). LCMS (M+H)=532.25.

Workup

  1. temperatureThen, cooled
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-96634c4074e74b21b2fa1fa8318124a3
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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