Tert-Butylamine → Methacrylic acid 1-tert-butylaminocarbonyl-1,1-difluoro-2-butyl ester

Reaction equation

[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(OC(C)C)(C)C.Cl[C:14]([C:16]([F:27])([F:26])[CH:17]([O:20][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[CH2:18][CH3:19])=[O:15]>>[C:1]([NH:5][C:14]([C:16]([F:26])([F:27])[CH:17]([O:20][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[CH2:18][CH3:19])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6385Tert-Butylamine

HCID 7914Diisopropyl Ether

HCID 58352381Methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl ester

Product 1

HCID 58571386Methacrylic acid 1-tert-butylaminocarbonyl-1,1-difluoro-2-butyl esterYield 112.7%

Procedure

In a 50-mL glass flask with a dropping funnel, 3.0 g (41.6 mmol/2.0 eq) of tertiary butylamine and 5.0 g of diisopropyl ether were added and stirred. Subsequently, 5.0 g (20.8 mmol) of methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl ester was dropped into the glass flask. The resulting solution was stirred for 10 minutes at room temperature. The completion of the reaction was confirmed by 19F NMR. After that, the solution was separated into an organic layer and an aqueous layer with the addition of 10 mL of water and 5 mL of diisopropyl ether. The thus-obtained organic layer was concentrated under a reduced pressure. With this, 6.5 g of methacrylic acid 1-tert-butylaminocarbonyl-1,1-difluoro-2-butyl ester was obtained as a white crystalline substance (yield: 99%, purity: 88%).