C-glycoside amine derivatives and methods of making

US11192913B2 · kind B2 · utility

Assignee

• The United States of America, as represented The Secretary of Agriculture · US

Inventors

• Michael Jackson · Morton, US
• Neil P. Price · Edelstein, US

Key dates

• Filing date: Jan 4, 2021
• Grant date: Dec 7, 2021
• Expiry date: Jan 4, 2041

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H1/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Disclosed are C-glycoside amine derivatives of the formula: R—CH2—C(CH3)—NH—R2 wherein R is a saccharide (e.g., as described in U.S. Pat. No. 8,314,219) and R2 is an acyl moiety derived from any ketone of the formula R3—C(O)—R3 wherein R3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. In addition, a method for making the C-glycoside amine derivatives involving (1) reacting a saccharide (e.g., glucose) C-glycoside ketone with a catalyst (e.g., Rh), about 10 to about 25 fold excess NH3, and an organic solvent (e.g., methanol) to form a saccharide C-glycoside amine, and (2) reacting said saccharide C-glycoside amine with a catalyst (e.g., Rh), an organic solvent (e.g., methanol), and an acyl moiety derived from any ketone of the formula R3—C(O)—R3 wherein R3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated to form said C-glycoside amine derivative.