1,2-Dichloroethane → HCID 56924314, compound

Boc-Ala-OH (14.24 g, 75.3 mmol), HOBT (1.35 g, 10 mmol), EDC (17.3 g, 90.4 mmol) and 2,2,2-trifluoroethylamine hydrochloride (10.2 g, 75.3 mmol) were dissolved in DMF (100 mL) using a water bath to maintain temperature. After the solids dissolved, triethylamine (20 mL, 150 mmol) was added and the resulting heterogeneous mixture stirred at room temperature overnight. The mixture was poured into ethylacetate (350 mL), washed with 1N HCl and brine then dried over Na2SO4. The solvent was removed under reduced pressure and the resulting oil dissolved in methanol (50 mL) and 2M HCl in ether (95 mL) then heated at 50° C. for 0.5 hours. The solvent was removed and the residue dried at 45° C. under vacuum to afford 12.2 g (78% yield) of the title compound (FF) as a white solid. FIA for C5H9F3N2O: 170.9 ES+.

1. temperatureto maintain temperature
2. dissolutionAfter the solids dissolved
3. washwashed with 1N HCl and brine
4. dry with materialthen dried over Na2SO4
5. customThe solvent was removed under reduced pressure
6. dissolutionthe resulting oil dissolved in methanol (50 mL)
7. temperature2M HCl in ether (95 mL) then heated at 50° C. for 0.5 hours
8. customThe solvent was removed
9. customthe residue dried at 45° C. under vacuum

ORD record

ord-da85e35e3c38454d849b72ad9fca3d78

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921376B2