Hydrochloric Acid → HCID 86597003, Verbindung

Temperatur

0 °C

To 25.00 g (137.62 mmol) of methyl(2S)-2-aminohexanoate hydrochloride in 458 mL of dichloromethane at 0° C. was added 44.52 mL (550.49 mmol) of pyridine. Then, 85.57 mL (165.14 mmol) of a 1.93 M solution of phosgene in toluene was added to the solution and the mixture was stirred at 0° C. for 3 h. The solution was poured into 1N hydrochloric acid at 0° C. and extracted with dichloromethane. The organic layer was washed with 1N hydrochloric acid and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by vacuum distillation at 80° C. @ 2 torr to give 21.32 g (91%) of methyl(2S)-2-isocyanatohexanoate. Rf=0.46 (1:4 ethyl acetate:hexanes); 1H NMR (300 MHz, DMSO-d6)δ 4.37 (dd, J=7 Hz, J=5 Hz, 1H), 3.73 (s, 3H), 1.78-1.60 (m, 2H), 1.36-1.16 (m, 4H), 0.85 (t, J=7 Hz, 3H); ES-MS m/z 172 (M+H).

1. extractionextracted with dichloromethane
2. washThe organic layer was washed with 1N hydrochloric acid and saturated sodium chloride
3. dry with materialThe organic layer was dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. distillationThe residue was purified by vacuum distillation at 80° C. @ 2 torr

ORD-Eintrag

ord-9e7916c3a4de4708944ed3bc6b39b6e1

Quelldatensatz

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07282512B2