Diisopropylamine → HCID 53386304, compound

Temperature

-10 °C

1000 mL THF and 132.27 g diisopropyl amine were taken in round bottom flask at 25° C. The reaction mixture was cooled to −10° C. and 531 mL of n-butyl amine was added to it. The reaction mixture was stirred for 30 minutes and further cooled to −40° C. 113 g N,N-dimethylacetamide solution in 1000 mL THF was gradually added to the reaction mixture and stirred for 2 hours. 100 g (S)-Ethyl-3-hydroxy-4-(1-phenyl-1H-tetrazol-5-ylthio)butanoate (11a) solution in 200 mL THF was added to the reaction mixture and stirred for 2 hours. After the completion of the reaction as monitored by TLC, the reaction mixture was quenched with 20% 1000 mL ammonium chloride solution at about −25° C. The separated aqueous layer was extracted with 400 mL ethyl acetate. The separated organic layer was washed with 1000 mL 1N HCl solution followed by washing with 1000 mL of water at 25° C. The organic layer was distilled under vacuum below 50° C. to obtain 100 g residue as an oil. The oily residue was taken in 400 mL hexane and distilled to obtain oil.

1. temperaturefurther cooled to −40° C
2. stirringstirred for 2 hours
3. stirringstirred for 2 hours
4. customAfter the completion of the reaction
5. customthe reaction mixture was quenched with 20% 1000 mL ammonium chloride solution at about −25° C
6. extractionThe separated aqueous layer was extracted with 400 mL ethyl acetate
7. washThe separated organic layer was washed with 1000 mL 1N HCl solution
8. washby washing with 1000 mL of water at 25° C
9. distillationThe organic layer was distilled under vacuum below 50° C.

ORD record

ord-6c3fd229872a47b8865db8eb589ab580

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759518B2