تفاعل #420216

معادلة التفاعل

HCl water

POCl3

calcium acetate monohydrate

(3S)-tetrahydro-3-furyl N-[(1S,2R)-1-benzyl-2-hydroxy-3-(N-isobutyl-4-nitrobenzene sulphonamido)propyl]carbamate

→

fosamprenavir calcium

المذيبات

methyl isobutyl ketone

water

pyridine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   درجة الحرارةMixture was heated to 50° C. for 1 hour
3. 3
   درجة الحرارةcooled to 25-30° C
4. 4
   أخرىOrganic layer was separated
5. 5
   غسيلwashed with water
6. 6
   تركيزpartially concentrated
7. 7
   workup.ADDITION500 ml water and 31.5 g sodium bicarbonate was added
8. 8
   workup.STIRRINGstirred
9. 9
   أخرىThe organic layer was separated
10. 10
    workup.ADDITION100 ml ethylacetate, 400 ml methanol and 5.0 g Pd/C was added
11. 11
    workup.STIRRINGThe reaction mass was stirred under hydrogen pressure for 4 hours at 30° C
12. 12
    ترشيحThe mixture was filtered
13. 13
    غسيلcatalyst washed with methanol
14. 14
    درجة الحرارةThe filtrate was heated to 50° C.
15. 15
    workup.STIRRINGstirred for 30 minutes
16. 16
    درجة الحرارةCooled to 30° C.
17. 17
    workup.STIRRINGstirred
18. 18
    ترشيحSolid was filtered
19. 19
    غسيلwashed with 1:1 mixture of methanol-water
20. 20
    أخرىdried

الإجراء التجريبي

Mixture of 100 g (0.186 mol) (3S)-tetrahydro-3-furyl N-[(1S,2R)-1-benzyl-2-hydroxy-3-(N-isobutyl-4-nitrobenzene sulphonamido)propyl]carbamate (IV) and 200 ml pyridine was cooled to 0-10° C. and 70.0 g (0.456 mol) of POCl3 was added and stirred at ambient temperature for 4 hours, 400 ml methyl isobutyl ketone was added, cooled and 1:1 conc. HCl-water was added. Mixture was heated to 50° C. for 1 hour, cooled to 25-30° C. Organic layer was separated, washed with water and partially concentrated; 500 ml water and 31.5 g sodium bicarbonate was added and stirred. The organic layer was separated and 100 ml ethylacetate, 400 ml methanol and 5.0 g Pd/C was added. The reaction mass was stirred under hydrogen pressure for 4 hours at 30° C. The mixture was filtered, catalyst washed with methanol. The filtrate was heated to 50° C. and 33.0 g (0.186 mol) calcium acetate monohydrate in 100 ml water was added and stirred for 30 minutes. Cooled to 30° C. and stirred. Solid was filtered, washed with 1:1 mixture of methanol-water and dried to obtain crude fosamprenavir calcium.

المصدر