Sodium Hydroxide → HCID 86658639, compound

Participants

Reaction Conditions

Reaction Steps

(S)-methyl 6-(4-acetylbenzamido)-2-(2,2,2-trifluoroacetamido)hexanoate (TU2982-136) (0.473 g) was treated 1 N aq NaOH (2.36 mL) in 10 mL MeOH at ambient temperature for 18 hours. LC-MS analysis was used to reveal the complete hydrolysis of the methyl ester, while maintaining the trifluoroamide moiety intact. The reaction was heated at 60° C. for 5 hours, at which time the amide hydrolysis was almost complete, as indicated by LC-MS analysis. The reaction mixture was cooled and concentrated under reduced pressure. The residue was treated with excess 1 N aq HCl, and concentrated to dryness under reduced pressure, affording ((S)-5-(4-acetylbenzamido)-1-carboxypentan-1-aminium chloride (TU3000-004) as a slightly yellow solid. MS (ESI+): calcd. 293.14. found 293.20 (MH+).

Provenance & Evidence