Sodium Hydroxide → 2-[(Morpholin-4-yl)methyl]-1,3-thiazole-4-carboxylic acid

HRID 244654Notes

Reaction equation

HRID 244654 reaction equation
[N:1]1([CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[N:1]1([CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13121935Ethyl 2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 391600072-[(Morpholin-4-yl)methyl]-1,3-thiazole-4-carboxylic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxylate (260 mg) was dissolved in methanol (5 ml). Sodium hydroxide (5 ml) was added and the mixture was stirred at RT for 18 h. The solvent was removed in vacuo and water (10 ml) added. The pH was adjusted to pH 5-6 by the addition of 2M hydrochloric acid. The aqueous layer was washed with DCM (3×25 ml). The aqueous layer was loaded onto a SCX SPE cartridge (20 g) and allowed to stand for 15 min. Elution with ethanol (100 ml) followed by 2M ammonia in ethanol (100 ml) gave the title compound (121 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo and water (10 ml)
  2. additionadded
  3. additionThe pH was adjusted to pH 5-6 by the addition of 2M hydrochloric acid
  4. washThe aqueous layer was washed with DCM (3×25 ml)
  5. waitto stand for 15 min
  6. washElution with ethanol (100 ml)

Sources & evidence

ORD record
ord-3ed14cfc045b4114bfbe343a8a5000ba
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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