Sodium Hydroxide → 2-(4-Hydroxy-piperidin-1-yl)-thiazole-4-carboxylic acid

HRID 1755218Notes

Reaction equation

HRID 1755218 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+].OS([O-])(=O)=O.[Na+]>CO>[OH:17][CH:14]1[CH2:15][CH2:16][N:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 22242823Ethyl 2-(4-hydroxypiperidin-1-yl)thiazole-4-carboxylate

Product 1

HCID 672705112-(4-Hydroxy-piperidin-1-yl)-thiazole-4-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-(4-hydroxy-piperidin-1-yl)-thiazole-4-carboxylic acid ethyl ester mixture from step a was dissolved in MeOH (10 mL). To this was added NaOH (2 M, 5.00 mL). The reaction mixture was stirred overnight, then diluted 1M NaHSO4 (30 mL). This solution was extracted with EtOAc (3×50 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated to give the product (433 mg, 1.90 mmol, 90%) as a white solid.

Workup

  1. extractionThis solution was extracted with EtOAc (3×50 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fccb14984ec645c4b50818eefee8de0f
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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