Cyclohexene → HCID 86723920, compound

To (R)-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionic acid methyl ester (172 g, 0.53 mol) was added 10% Pd/C (8.6 g), MeOH (530 mL) and cyclohexene (344 mL) under nitrogen. The mixture was heated to reflux for 17 h. MeOH (500 mL) was added and the reflux continued for 1 h. The hot reaction mixture was filtered through a pad of celite, cake washing with hot MeOH (2×500 mL). The combined filtrates were concentrated. The resulting solid was slurried in 2-butanone (400 mL) and petrol (400 mL) was added gradually over 10 min. After stirring for 30 min, the solids were filtered, cake washed with 2:1 petrol/2-butanone (300 mL). The filter cake was dried in vacuo at 40° C., to give the title compound (68.3 g) as an off white solid. 1H NMR (DMSO-d6): 8.08 (1H, s), 7.90 (1H, s), 5.11 (1H, t), 3.92 (1H, q), 3.80-3.71 (1H, m), 3.71-3.60 (1H, m), 3.58-3.47 (1H, m), 1.24 (3H, d).

1. temperatureThe mixture was heated
2. temperatureto reflux for 17 h
3. filtrationThe hot reaction mixture was filtered through a pad of celite, cake
4. washwashing with hot MeOH (2×500 mL)
5. concentrationThe combined filtrates were concentrated
6. additionpetrol (400 mL) was added gradually over 10 min
7. filtrationthe solids were filtered
8. washcake washed with 2:1 petrol/2-butanone (300 mL)
9. customThe filter cake was dried in vacuo at 40° C.

ORD record

ord-f01bec7b96e14e9db0d965c1bf69b02a

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018214B2