Heptane → HCID 86601560, compound

Temperature

37 °C

A suspension of the product of Example 61 c) (4573 g, 7.47 mol) in acetonitrile (4 L) was added to a 50 L reactor equipped with a thermocouple and nitrogen inlet. An additional 13 L of acetonitrile was added and the suspension was heated to 37° C. with steam. A solution of triflic acid (1253 mL, 14.16 mol) in water (7.6 L) was added over 20 minutes. Then the mixture was stirred at 39–42° C. for 1 hour. The reaction mixture was quenched by adding it to 20 L of 23% aqueous sodium bicarbonate solution and 35 L of methyl t-butyl ether. The reaction flask was rinsed with 5 L of methyl t-butyl ether and an additional 20 L of 23% aqueous sodium bicarbonate was addded. This mixture was stirred for 10 minutes and the layers were separated. The organic layer was washed with a mixture of 25 L of 23% aqueous sodium bicarbonate solution and 15 L of 7% NaCl solution. Then the organic layer was washed with 25 L of 7% NaCl solution. The solvents were removed on a batch concentrator to provide a thick slurry. Heptane (32 L) was added to the slurry and then evaporated. Additional heptane (12 L) was added and evaporated. A further amount of heptane (40 L) was added and the suspensin was heated to 44° C. in 60 minutes, causing complete dissolution. The reaction flask was cooled to 40° C. in 10 minutes by running cold water over the surface of the flask. The solution was then allowed to slowly cool to 35° C., where cyrstallization occurs. The resulting thick mixture was stirred for 14 hours. The precipitate was filtered and rinsed twice with 4 L of heptane and then dried on the filter funnel for 2 hours and then in a vacuum oven with nitrogen purge for 60 hours at room temperature. The resulting solid (3200 g), heptane (30 L) and methyl t-butyl ether (1.6 L) were combined and heated with stirring to dissolution. The resulting solution was cooled over 1 hour to 42° C. and the resulting suspension was stirred for 20 hours while cooling to room temperature. The precipitate was filtered and dried in a vacuum oven with nitrogen purge for 20 hours at room temperature to give the desired product (2860 g).

1. additionwas added to a 50 L reactor
2. customequipped with a thermocouple and nitrogen inlet
3. customThe reaction mixture was quenched
4. additionby adding it to 20 L of 23% aqueous sodium bicarbonate solution and 35 L of methyl t-butyl ether
5. washThe reaction flask was rinsed with 5 L of methyl t-butyl ether
6. stirringThis mixture was stirred for 10 minutes
7. customthe layers were separated
8. washThe organic layer was washed with a mixture of 25 L of 23% aqueous sodium bicarbonate solution and 15 L of 7% NaCl solution
9. washThen the organic layer was washed with 25 L of 7% NaCl solution
10. customThe solvents were removed on a batch concentrator
11. customto provide a thick slurry
12. customevaporated
13. additionAdditional heptane (12 L) was added
14. customevaporated
15. additionA further amount of heptane (40 L) was added
16. temperaturethe suspensin was heated to 44° C. in 60 minutes
17. dissolutiondissolution
18. temperatureThe reaction flask was cooled to 40° C. in 10 minutes
19. temperatureto slowly cool to 35° C.
20. stirringThe resulting thick mixture was stirred for 14 hours
21. filtrationThe precipitate was filtered
22. washrinsed twice with 4 L of heptane
23. customdried on the filter funnel for 2 hours
24. customin a vacuum oven with nitrogen purge for 60 hours at room temperature
25. temperatureheated
26. stirringwith stirring to dissolution
27. temperatureThe resulting solution was cooled over 1 hour to 42° C.
28. stirringthe resulting suspension was stirred for 20 hours
29. temperaturewhile cooling to room temperature
30. filtrationThe precipitate was filtered
31. customdried in a vacuum oven with nitrogen
32. custompurge for 20 hours at room temperature

ORD record

ord-5f5355deb4cf49b58146a4d7f2342fce

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189849B2