Lithium Hydroxide → HCID 118307733, compound

HRID 718431Notes

Reaction equation

HRID 718431 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:36])=[N:14][C:15]([CH3:35])=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[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].[Li+].[OH-]>CCO.O>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:36])=[N:14][C:15]([CH3:35])=[C:16]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH3:34])=[CH:30][CH:31]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:24])([CH3:25])[CH2:20][CH2:19]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118314206HCID 118314206, compound

Product 1

HCID 118307733HCID 118307733, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-ethoxyphenyl)-2,6-dimethylpyridin-3-yl)acetate (0.013 g, 0.026 mmol) and LiOH (6.27 mg, 0.262 mmol) in 9:1 EtOH/H2O (1 ml) was refluxed for 3 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-ethoxyphenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0105 g, 0.022 mmol, 86% yield) as solid. 1H NMR (500 MHz, CDCl3) δ 7.12-7.17 (m, 1H), 7.03-7.07 (m, 1H), 6.95-7.01 (m, 2H), 5.90 (br. s., 1H), 4.06-4.17 (m, 2H), 3.46-3.88 (m, 1H), 2.75-3.08 (m, 1H), 2.70 (s, 3H), 2.25 (s, 3H), 1.91-2.43 (m, 2H), 1.48 (t, J=7.0 Hz, 3H), 1.13-1.37 (m, 4H), 1.25 (s, 9H), 0.78 (br.s., 6H). LCMS (M+H)=469.3.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperatureThen, cooled
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-2f68f6dd25b34d4aa6569db084fb419f
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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