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

HRID 2390543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390543
[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

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 235881312-(Hydroxymethyl)thiazole-4-carboxylic acid

Produkt 1

HCID 288755532-(Methoxymethyl)-1,3-thiazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-88cbdd559fde4befb19df9930a513371
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273774B2

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