4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 54023959, compound

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Reaction Steps

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (18.1 g) is added to a solution of ethyl (2-aminothiazol-4-yl)acetate (10 g) in pyridine (300 cc). After 48 hours at a temperature of the order of 20° C., the solution is concentrated to dryness under reduced pressure (25 mm Hg; 3.3. kPa) at 60° C. The residue is dissolved in a mixture of methylene chloride (200 cc) and N sodium hydroxide solution (100 cc). The organic phase is decanted off, washed with water (3×100 cc), dried over sodium sulphate and then concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C. The residue is recrystallised by dissolving it in boiling acetonitrile (100 cc) and then cooling. The crystals formed are filtered off, washed with acetonitrile (20 cc) and then with diethyl ether (20 cc) and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(4-ethoxycarbonylmethylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (11.7 g), m.p.=105° C.

Provenance & Evidence