Citric Acid → HCID 86741585, compound

Temperature

20 °C

53.5 g of 2-methoxy-5-methyl sulfinyl benzoic acid, 740 ml of acetone, 140 ml of water and 35 ml of triethylamine (density 0.726) are placed in a 2 liter flask fitted with an agitator, a thermometer and a dropping funnel. The solution is cooled to between 0° and +5° C., after which 34.1 g of isobutyl chloroformate is dripped in. The mixture is agitated for 45 minutes at 20° C. then cooled to 0° C., and 42 g of 1-cyclopropyl-2-amino methyl pyrrolidine is poured in drop by drop. The mixture is reacted at room temperature then left to stand. The solvents are evaporated under vacuum. The oily residue is dissolved in 250 ml of water and 50 ml of hydrochloric acid (density 1.18) and extracted twice with 125 ml of methylene chloride. The aqueous phase is then made alkaline with 70 ml of soda lye. A yellow oil is salted out. It is extracted 3 times with 250 ml of methylene chloride and the organic phase is washed 3 times with 100 ml of water and dried over magnesium sulphate. The solution is filtered and the solvent evaporated. An oily residue is obtained. It is dissolved in 500 ml of ethanol and an equimolar quantity of citric acid is added. It is evaporated under vacuum and the residue is dissolved in 1,000 ml of boiling isopropanol then cooled. The supernatant solution is decanted off and the residual paste dissolved in 600 ml of water. The solution is filtered with charcoal then the filtrate is evaporated under vacuum.

1. customfitted with an agitator
2. temperatureThe solution is cooled to between 0° and +5° C.
3. temperaturethen cooled to 0° C.
4. customThe mixture is reacted at room temperature
5. waitthen left
6. customThe solvents are evaporated under vacuum
7. dissolutionThe oily residue is dissolved in 250 ml of water
8. extraction50 ml of hydrochloric acid (density 1.18) and extracted twice with 125 ml of methylene chloride
9. extractionIt is extracted 3 times with 250 ml of methylene chloride
10. washthe organic phase is washed 3 times with 100 ml of water
11. dry with materialdried over magnesium sulphate
12. filtrationThe solution is filtered
13. customthe solvent evaporated
14. customAn oily residue is obtained
15. customIt is evaporated under vacuum
16. dissolutionthe residue is dissolved in 1,000 ml of boiling isopropanol
17. temperaturethen cooled
18. customThe supernatant solution is decanted off
19. dissolutionthe residual paste dissolved in 600 ml of water
20. filtrationThe solution is filtered with charcoal
21. customthe filtrate is evaporated under vacuum

ORD record

ord-d6b1590e657044bfa3931ad25e06827b

Source dataset

uspto-grants-1987_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04673686