Sodium Hydroxide → HCID 118307794, compound

HRID 718458Notes

Reaction equation

HRID 718458 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[C:17]([N:35]3[CH2:40][CH2:39][C:38]([CH3:42])([CH3:41])[CH2:37][CH2:36]3)=[C:18]([C@H:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:27]CC)=[O:26])[C:19]([CH3:23])=[N:20][C:21]=2[CH3:22])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[C:17]([N:35]3[CH2:36][CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][CH2:40]3)=[C:18]([C@H:24]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])[C:25]([OH:27])=[O:26])[C:19]([CH3:23])=[N:20][C:21]=2[CH3:22])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118314214HCID 118314214, compound

Product 1

HCID 118307794HCID 118307794, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-ethyl 2-(5-(3-(benzyloxy)-4-methylphenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.0121 g, 0.021 mmol) and 1M NaOH (0.211 ml, 0.211 mmol) in EtOH (1 mL) was refluxed for 6 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(5-(3-(benzyloxy)-4-methylphenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetic acid (0.0103 g, 0.019 mmol, 90% yield) as solid and ˜3:2 mixture of isomers by H-NMR. LCMS (M+H)=545.25.

Workup

  1. temperatureThen, cooled
  2. custompurified by prep-HPLC
  3. customto afford

Sources & evidence

ORD record
ord-f1aab3c98ee24a809d285b0e2d111fa1
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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