Lithium Hydroxide → HCID 118307806, compound

HRID 718430Notes

Reaction equation

HRID 718430 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:42])=[N:14][C:15]([CH3:41])=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[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].[Li+].[OH-]>CCO.O>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:42])=[N:14][C:15]([CH3:41])=[C:16]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=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 3939Lithium HydroxideHCID 118314210HCID 118314210, compound

Product 1

HCID 118307806HCID 118307806, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(5-(4-((4-chlorobenzyl)oxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (0.0344 g, 0.058 mmol) and LiOH (0.014 g, 0.580 mmol) in 9:1 EtOH/H2O (2 mL0 was refluxed for 3 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(5-(4-((4-chlorobenzyl)oxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0258 g, 0.046 mmol, 79% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.38-7.44 (m, 4H), 7.15-7.20 (m, 1H), 7.01-7.10 (m, 3H), 5.99 (br. s., 1H), 5.08-5.16 (m, 2H), 3.57 (br. s., 1H), 2.90 (br. s., 1H), 2.64 (s, 3H), 2.24-2.32 (m, 1H), 2.22 (s, 3H), 1.97-2.13 (m, 1H), 1.25 (s, 9H), 0.88 (br.s., 3H), 0.64 (br. s., 3H). 4H of piperidine were not resolved. LCMS (M+H)=565.3.

Workup

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

Sources & evidence

ORD record
ord-42c20692a3c04afa9d7d512d06a23ede
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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