Sodium Hydroxide → HCID 118129974, compound

HRID 2272841Notes

Reaction equation

HRID 2272841 reaction equation
C([O:3][C:4](=[O:43])[CH2:5][C@@H:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[N:22]([N:24]=[C:25]([C:27]4[C:32]([CH3:33])=[CH:31][C:30]([O:34][CH2:35][CH2:36][CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:29][C:28]=4[CH3:42])[N:26]=3)[CH:23]=2)=[CH:12][CH:11]=1)[C:7]#[C:8][CH3:9])C.[OH-].[Na+]>CCO>[CH3:42][C:28]1[CH:29]=[C:30]([O:34][CH2:35][CH2:36][CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:31]=[C:32]([CH3:33])[C:27]=1[C:25]1[N:26]=[C:21]2[CH:20]=[CH:19][C:18]([CH2:17][O:16][C:13]3[CH:12]=[CH:11][C:10]([C@@H:6]([C:7]#[C:8][CH3:9])[CH2:5][C:4]([OH:43])=[O:3])=[CH:15][CH:14]=3)=[CH:23][N:22]2[N:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118129984HCID 118129984, compound

Product 1

HCID 118129974HCID 118129974, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)-3-(4-{2-[4-(3-methanesulfonyl-propoxy)-2,6-dimethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy}-phenyl)-hex-4-ynoic acid ethyl ester (0.145 g, 0.238 mmol) in EtOH (5 mL) is added 5 N NaOH solution (0.14 mL, 0.715 mmol) at room temperature and the reaction mixture is heated at 50° C. for 30 minutes. The reaction mixture is evaporated and the residue is dissolved in water (5 mL), washed with ether (2×5 mL), and acidified with aqueous citric acid solution (pH-6) at 0° C. The precipitate solid is filtered and dried to give the title compound as an off-white solid (0.075 g, 55%). LCMS m/z 576 [M+H]+.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in water (5 mL)
  3. washwashed with ether (2×5 mL)
  4. customacidified with aqueous citric acid solution (pH-6) at 0° C
  5. filtrationThe precipitate solid is filtered
  6. customdried

Sources & evidence

ORD record
ord-3ca264b2600c49d584038657a76433a6
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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