Sodium Hydroxide → 2-(Hydroxymethyl)thiazole-4-carboxylic acid

HRID 2390541Notes

Reaction equation

HRID 2390541 reaction equation
[OH-].[Na+].C([O:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([O:18]CC)=[O:17])[N:15]=1)(=O)C(C)(C)C>O.C1COCC1.CO>[OH:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67025585Ethyl 2-(pivaloyloxymethyl)thiazole-4-carboxylate

Product 1

HCID 235881312-(Hydroxymethyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of NaOH (1.769 g, 44.23 mmol) in water (20.0 mL) was added to a stirred solution of ethyl 2-(pivaloyloxymethyl)thiazole-4-carboxylate (2.4 g, 8.85 mmol) in a mixture of THF (20 mL) and MeOH (10.0 mL), and the reaction stirred for 72 h. Acidified with 2M HCl (10 mL) and evaporated in vacuo to afford crude 2-(hydroxymethyl)thiazole-4-carboxylic acid as a white solid. Purified by reverse phase chromatography with MeCN/aqTFA as eluent to afford the sub-title compound as a white solid. Yield: 1.4 g

Workup

  1. customAcidified with 2M HCl (10 mL) and evaporated in vacuo
  2. customto afford crude 2-(hydroxymethyl)thiazole-4-carboxylic acid as a white solid
  3. customPurified by reverse phase chromatography with MeCN/aqTFA as eluent

Sources & evidence

ORD record
ord-650ce7c182f641dcaf2bc198af64f523
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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