反应详情

温度

42.5 °C

(1S,2R)-{1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester (3, 100 g), 10% palladium carbon (10 gm) and triethanolamine (2 gm) were suspended in isopropyl alcohol. The reaction was heated to 40-45° C. and maintained under 4-6 kg/cm2 of hydrogen pressure for 3 hours. After completion of reaction, the mass was filtered and hydrochloric acid (70 mL) was added to the filtered mass. The solution was heated to reflux and maintained for 2-3 hours. After completion of reaction the mass was cooled to 25-35° C., the reaction mass pH was adjusted to 6.0-7.0 with 20% sodium hydroxide solution and distilled out isopropyl alcohol under vacuum at below 55° C. Ethanol (200 mL) and water (400 mL) was added to the distillate, the mass pH was adjusted to 9.0-10.0 with 20% sodium hydroxide solution at 25-35° C. and maintained the stirring for 2 hours at 25-35° C. The mass was cooled to 0-5° C., filtered and wash with water. The wet product was taken into ethanol (350 mL), maintained the stirring for 30 minutes at reflux temperature. The mass was cooled to 2-4° C., stirred for 2 hours, filtered and washed with ethanol (50 mL). The wet product was dried under normal drying to get title compound 1 (Yield 60 g).

1. customAfter completion of reaction
2. filtrationthe mass was filtered
3. additionhydrochloric acid (70 mL) was added to the filtered mass
4. temperatureThe solution was heated
5. temperatureto reflux
6. temperaturemaintained for 2-3 hours
7. customAfter completion of reaction the mass
8. temperaturewas cooled to 25-35° C.
9. distillationdistilled out isopropyl alcohol under vacuum at below 55° C
10. additionEthanol (200 mL) and water (400 mL) was added to the distillate
11. customwas adjusted to 9.0-10.0 with 20% sodium hydroxide solution at 25-35° C.
12. temperaturemaintained the stirring for 2 hours at 25-35° C
13. temperatureThe mass was cooled to 0-5° C.
14. filtrationfiltered
15. washwash with water
16. temperaturemaintained the stirring for 30 minutes
17. temperatureat reflux temperature
18. temperatureThe mass was cooled to 2-4° C.
19. filtrationfiltered
20. washwashed with ethanol (50 mL)
21. customThe wet product was dried
22. customunder normal drying