Hydrochloric Acid → 2-(Methoxymethyl)-1,3-thiazole-4-carboxylic acid

HRID 2390543Notes

Reaction equation

[H-].[Na+].[OH:3][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1.[CH3:13]I.[OH-].[Na+].Cl>CN(C=O)C.O>[CH3:13][O:3][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (0.151 g, 3.77 mmol) was added to a solution of 2-(hydroxymethyl)thiazole-4-carboxylic acid (0.2 g, 1.26 mmol) in DMF (2 mL) and stirred for 20 min. Methyl iodide (0.236 mL, 3.77 mmol) was added and the reaction stirred for a further 2 h. Water (2 mL) was added, followed by NaOH (0.251 g, 6.28 mmol) and stirred for 20 h. The reaction mixture was heated at 60° C. for 5 h then cooled to RT, acidified with 2M HCl and purified by reverse phase HPLC with MeCN/aqTFA as eluent to afford the sub-title compound as a white solid. Yield: 31 mg

Workup

stirringthe reaction stirred for a further 2 h
stirringstirred for 20 h
temperaturethen cooled to RT
custompurified by reverse phase HPLC with MeCN/aqTFA as eluent

Sources & evidence

ORD record: ord-88cbdd559fde4befb19df9930a513371
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273774B2

Reaction notes

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