Triethylamine → HCID 11240761, compound

(3R,4R,5R)-3-Amino-4,5-dimethyl-heptanoic acid hydrochloride (10.8 g, 51.5 mmol) was dissolved in 50 mL of methanol. To this solution was added triethylamine (5.2 g, 7.2 mL, 51.5 mmol). The solution was stirred for 10 minutes and then evaporated to a flocculent solid. Dichloromethane (376 mL) was added and the resulting slurry was stirred at room temperature for 45 minutes. Next, 188 mL of acetonitrile was added and the slurry was stirred for 30 minutes and then filtered. The solids were washed with 20 mL of 2:1 (v/v) dichloromethane-acetonitrile and dried on a nitrogen press to give 7.64 g (85.6% yield) of the titled compound as a white solid: 1H NMR (CD3OD, 399.77 MHz) 0.88 (t, J=7.5 Hz, 3H), 0.91 (d, J=7.0 Hz, 3H), 0.94 (d, J=6.6 Hz, 3H), 0.98-1.12 (m, 1H), 1.32-1.43 (m, 1H), 1.43-1.64 (m, 2H), 2.26 (dd, J=16.5, 9.9 Hz, 1H), 2.47 (dd, J=9.5, 3.7 Hz, 1H), 3.28-3.36 (m, 1H). Low resolution mass spec: nominal m/e calc'd for C9H19NO2 (M+H)+: 174. Found: m/e 174.

1. customevaporated to a flocculent solid
2. additionDichloromethane (376 mL) was added
3. stirringthe resulting slurry was stirred at room temperature for 45 minutes
4. additionNext, 188 mL of acetonitrile was added
5. stirringthe slurry was stirred for 30 minutes
6. filtrationfiltered
7. washThe solids were washed with 20 mL of 2:1 (v/v) dichloromethane-acetonitrile
8. customdried on a nitrogen press

ORD record

ord-7dc9a0458aa3499bb0a8ede2355f9222

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07388023B2