反应详情

A suspension of NaH (0.24 g, 0.006 mol) in THF (30 mL) was treated with 1-t-butylcarbamoyl-3-hydroxyazetidine (1.1 g, 0.006 mol), the reaction stirred 1 h, followed by addition of 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1.0 g, 0.0042 mol) in THF (5 mL). The reaction was heated to reflux for 4 h, the solvent evaporated, the residue treated with ice-water, and the mixture extracted with EtOAc. The extracts were dried and treated with a slow stream of HCl for 3 min. After 0.5 h, the solvent was evaporated, the residue treated with ice-water, and the solution extracted with ether. The aqueous phase was made basic, extracted with EtOAc, the extracts washed with brine, dried, and the solvent evaporated to give a clear oil. The HCl salt (0.77 g) crystallized from 2-propanol, m.p. 167°-168.5° C. (Compound 50).

1. temperatureThe reaction was heated
2. temperatureto reflux for 4 h
3. customthe solvent evaporated
4. additionthe residue treated with ice-water
5. extractionthe mixture extracted with EtOAc
6. customThe extracts were dried
7. additiontreated with a slow stream of HCl for 3 min
8. waitAfter 0.5 h
9. customthe solvent was evaporated
10. additionthe residue treated with ice-water
11. extractionthe solution extracted with ether
12. extractionextracted with EtOAc
13. washthe extracts washed with brine
14. customdried
15. customthe solvent evaporated
16. customto give a clear oil
17. customThe HCl salt (0.77 g) crystallized from 2-propanol, m.p. 167°-168.5° C. (Compound 50)