Hydrochloric Acid → (1S)-4-amino-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]1-isopropylcyclopent-2-ene-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of (1S)—N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxamide (46 g, 97 mmol),hydroxyanime HCl (41 g, 580 mmol), and hydroxyamine (50% in H2O, 50 mL) in MeOH:H2O (2:1, 450 mL) was heated to 70° C. for 11 hr until no more starting material left as judged by HPLC. The reaction mixture was then cooled to r. t., the pH was adjusted to 11.0 with 1 N NaOH, and it was diluted with EtOAc. The aqueous phase was then extracted with EtOAc (5×). The organics were then combined, dried over sodium sulfate and evaporated to dryness to give 35 g of (1S)-4-amino-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropylcyclopent-2-ene-1-carboxamide as a yellow oil that crystallized upon standing.

Provenance & Evidence