Acetic Anhydride → HCID 178472021, compound

Reaction equation

[O:1]=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=1[F:19])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:20](OC(=O)C)(=O)C.C(OCC)(OCC)OCC.[F:37][C:38]([F:42])([F:41])[CH2:39][NH2:40]>>[F:37][C:38]([F:42])([F:41])[CH2:39][NH:40][CH:20]=[C:3]([C:2](=[O:1])[C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=1[F:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 9773Ethanamine, 2,2,2-trifluoro-

HCID 31214Ethyl orthoformate

HCID 10588473Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate

Product 1

HCID 178472021HCID 178472021, compound

Procedure

2.00 g (5.79 mmol) of ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate (for preparation see Journal of Medicinal Chemistry (1995), 38 (22), 4478-87) are stirred under reflux in 3.8 ml (4.14 g, 40.55 mmol) of acetic anhydride and 4.82 ml (4.29 g, 28.96 mmol) of triethyl orthoformate for 2 h. The solvent is then removed completely on a rotary evaporator and the residue is dissolved in 10 ml of ethanol. 1.03 g (10.43 mmol) of 2,2,2-trifluoro-1-aminoethane are added dropwise to the ice-cooled solution. The mixture is brought to room temperature and stirred at that temperature overnight. For the work up, the solvent is removed and the residue is reacted further as a crude product without purification steps (yield assumed to be quantitive).