Sodium Hydroxide → Unii-2OH4ruc1V4

HRID 2272840Notes

Reaction equation

HRID 2272840 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:35]=[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C@@H:25]([C:32]#[C:33][CH3:34])[CH2:26][C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=3)=[CH:16][N:11]2[N:10]=1.[OH-].[Na+]>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:35]=[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([C@@H:25]([C:32]#[C:33][CH3:34])[CH2:26][C:27]([OH:29])=[O:28])=[CH:23][CH:24]=3)=[CH:16][N:11]2[N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118151368Ethyl (3S)-3-[4-[[2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoate

Product 1

HCID 91809187Unii-2OH4ruc1V4Yield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl (3S)-3-[4-[[2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoate (0.22 g, 0.47 mmol) in EtOH (20 mL) is added 5 N NaOH (0.3 mL) and the reaction mixture is stirred at 80° C. in a microwave instrument for 30 minutes. The reaction mixture is evaporated to dryness, diluted with water, and acidified with 6 N HCl solution to pH ˜3. The precipitated solid is filtered, washed with n-pentane, and dried to give the title compound as a white solid (0.155 g, 75%). LCMS m/z 440 (M+H)+.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. additiondiluted with water
  3. filtrationThe precipitated solid is filtered
  4. washwashed with n-pentane
  5. customdried

Sources & evidence

ORD record
ord-142fb4cc3e3446139a5a784ace6177c5
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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