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

5-Bromo-2-aminothiazole (25 g, 96 mmol) in DMF (150 mL) was added K2CO3 (26.5 g, 192 mmol) and the mixture was purged with N2 for 5 min. The mixture was cooled to 0° C. on an ice bath before 3-mercaptopropionic acid ethyl ester (12.9 g, 96 mmol) was added dropwise over the course of 30 min. The reaction mixture was stirred for 16 hours before water (400 mL) was added. The aqueous mixture was extracted with Et2O (1×500 mL, 2×250 mL). The combined organic phases was washed with saturated NH4Cl (3×150 mL), dried (MgSO4). The solvent was removed in vacuo to give a dark residue which was purified by column chromatography (SiO2, EtOAc-heptane (1:1)). The solvent was removed in vacuo to give 11 g (49%) of the desired compound.

1. customthe mixture was purged with N2 for 5 min
2. additionwas added dropwise over the course of 30 min
3. additionwas added
4. extractionThe aqueous mixture was extracted with Et2O (1×500 mL, 2×250 mL)
5. washThe combined organic phases was washed with saturated NH4Cl (3×150 mL)
6. dry with materialdried (MgSO4)
7. customThe solvent was removed in vacuo
8. customto give a dark residue which
9. customwas purified by column chromatography (SiO2, EtOAc-heptane (1:1))
10. customThe solvent was removed in vacuo

ORD record

ord-9985b0566eaa4679be131604ba410710

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884210B2