Tert-butoxycarbonylalanine → HCID 178462194, Verbindung

Temperatur

0 °C

A mixture of N2-(trans-3-benzyloxycyclobutyl)-4-fluoro-benzene-1,2-diamine (1.73 g, 2.55 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (0.54 g, 2.81 mmol) and HOAt (0.38 g, 2.81 mmol) in DCM (20 mL) were cooled to 0° C. under nitrogen atmosphere. To this mixture N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (0.54 g, 2.81 mmol) was added portion wise and the reaction mixture was stirred at RT for 1 h. The reaction mixture allowed to warm to RT then partitioned between DCM (30 mL) and 10% aqueous citric acid (20 mL). The organic layer was washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane) to afford the title compound as a off-white gum, which solidified on standing (0.88 g, 75%). NMR: 328289. LCMS (Method B): RT 3.85 min [M+H]+ 458.

1. temperatureto warm to RT
2. customthen partitioned between DCM (30 mL) and 10% aqueous citric acid (20 mL)
3. washThe organic layer was washed with brine (20 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane)

ORD-Eintrag

ord-772a8c73e9db4872b26723aea794dc7b

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08653089B2