Potassium Carbonate → Ethyl 3-[(2-amino-1,3-thiazol-5-YL)sulfanyl]propanoate

To a solution of 2-amino-5-bromothiazole (50 g, 192 mmol) in DMF (300 mL) were added potassium carbonate (53 g, 384 mmol) and ethyl 3-mercaptopropionate (25.8 g, 192 mmol). The reaction mixture was stirred at room temperature for 36 h. The mixture was partitioned between water (500 mL) and ethyl acetate (500 mL) and the isolated water phase was extracted with ethyl acetate (250 mL). The combinde organic phases were washed with water (250 mL) and 10% aqueous sodium hydrogencarbonate (250 mL), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo to give 3-(2-amino-thiazol-5-ylsulfanyl)-propionic acid ethyl ester. Yield: 19.6 g (44%). 1H-NMR (CDCl3): δ 7.07 (s, 1H); 4.15 (q, 2H); 2.88 (t, 2H); 2.61 (t, 2H); 1.26 (t, 3H); HPLC-MS: m/z: 233 (M+1).

1. customThe mixture was partitioned between water (500 mL) and ethyl acetate (500 mL)
2. extractionthe isolated water phase was extracted with ethyl acetate (250 mL)
3. washThe combinde organic phases were washed with water (250 mL) and 10% aqueous sodium hydrogencarbonate (250 mL)
4. dry with materialdried over anhydrous magnesium sulphate
5. customevaporated to dryness in vacuo

ORD record

ord-52e1f75ec4a54f05aa46069148dbedef

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148412B2