Lithium Hydroxide → HCID 118307833, compound

HRID 718425Notes

Reaction equation

HRID 718425 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([N:34]3[CH2:39][CH2:38][C:37]([CH3:41])([CH3:40])[CH2:36][CH2:35]3)=[C:17]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26]CC)=[O:25])[C:18]([CH3:22])=[N:19][C:20]=2[CH3:21])=[CH:11][C:10]=1[F:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CCO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([N:34]3[CH2:35][CH2:36][C:37]([CH3:41])([CH3:40])[CH2:38][CH2:39]3)=[C:17]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([OH:26])=[O:25])[C:18]([CH3:22])=[N:19][C:20]=2[CH3:21])=[CH:11][C:10]=1[F:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118314218HCID 118314218, compound

Product 1

HCID 118307833HCID 118307833, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of (S)-ethyl 2-(5-(4-(benzyloxy)-3-fluorophenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.019 g, 0.033 mmol) and LiOH (7.89 mg, 0.329 mmol) in 9:1 EtOH/H2O (2 mL) was refluxed for 3 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(5-(4-(benzyloxy)-3-fluorophenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetic acid (0.0162 g, 0.030 mmol, 90% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.47-7.51 (m, 2H), 7.42 (dt, J=3.0, 7.3 Hz, 2H), 7.34-7.39 (m, 1H), 7.08 (t, J=8.4 Hz, 1H), 7.03 (dd, J=1.9, 11.5 Hz, 0.5H), 6.89-6.94 (m, 1H), 6.80 (d, J=8.2 Hz, 0.5H), 5.83 (br. s., 0.6H), 5.78 (br. s., 0.4H), 5.18-5.26 (m, 2H), 2.74 (s, 1.3H), 2.72 (s, 1.7H), 2.27 (s, 1.7H), 2.26 (s, 1.3H), 1.26-1.39 (m, 4H), 1.23 (s, 9H), 0.82 (br. s., 6H). 4H of piperidine were not resolved. LCMS (M+H)=549.47.

Workup

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

Sources & evidence

ORD record
ord-ecaf7ae32ea444dc9adee61682229439
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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