Triethylamine → HCID 57935243, compound

Dicyclohexyl carbodiimide (9.51 g, 46.1 mmol), N,N′-dimethyl-4-aminopyridine (1.13 g, 9.2 mmol) and triethylamine (6.4 ml, 46.1 mmol) were added to a solution of Meldrum's acid (6.64 g, 46.1 mmol) in dichloromethane (150 ml). (4R)-4-Methylhexanoic acid (6 g, 46.1 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was filtered and the solid was washed with dichloromethane (2×100 ml). The filtrate and washings were combined and evaporated under reduced pressure to give an orange oil. Acetic acid (50 ml) and water (50 ml) were added and the reaction was heated under reflux overnight. After the solution had cooled to room temperature it was extracted with pentane (100 ml). The organic extract was dried (MgSO4) and evaporated to give a residue that was purified by column chromatography on silica gel using an elution gradient of pentane to pentane:diethyl ether 19:1 to give the title compound (2.8 g) as a pale yellow oil.

1. filtrationThe reaction mixture was filtered
2. washthe solid was washed with dichloromethane (2×100 ml)
3. customevaporated under reduced pressure
4. customto give an orange oil
5. temperaturethe reaction was heated
6. temperatureunder reflux overnight
7. extractionwas extracted with pentane (100 ml)
8. extractionThe organic extract
9. dry with materialwas dried (MgSO4)
10. customevaporated
11. customto give a residue that
12. customwas purified by column chromatography on silica gel using an elution gradient of pentane to pentane:diethyl ether 19:1

ORD record

ord-9a327db5d1dc4be4bee4597523a5ffbf

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612226B2