Trifluoroacetic acid → (S)-2-amino-N-{(S)-1-[(S)-1-benzyl-2-((R)-2-methyl-oxiranyl)-2-oxo-ethylcarbamoyl]-2-difluoromethoxy-ethyl}-3-difluoromethoxy-propionamide TFA salt

Participants

Reaction Steps

To a solution of the compound of Formula XIV(a), ((S)-1-{(S)-1-[(S)-1-benzyl-2-((R)-2-methyl-oxiranyl)-2-oxo-ethylcarbamoyl]-2-difluoromethoxy-ethylcarbamoyl}-2-difluoromethoxy-ethyl)-carbamic acid tert-butyl ester (2.68 g, 4.62 mmol) in dichloromethane (10 mL) at 0° C. was added TFA (10 mL), and the resulting mixture was stirred for 1 hr. Excess TFA was evaporated to dryness, and the residue obtained was triturated with ether in hexanes (2×20 mL) to provide the compound of Formula XV(a), (S)-2-amino-N—{(S)-1-[(S)-1-benzyl-2-((R)-2-methyl-oxiranyl)-2-oxo-ethylcarbamoyl]-2-difluoromethoxy-ethyl}-3-difluoromethoxy-propionamide TFA salt (2.34 g, 85%), as a pale-yellow solid. 1H NMR (300 MHz, d6-DMSO): δ (ppm) 7.42-7.32 (m, 3H), 7.23 (dd, 2H), 6.85 (wd, 1H), 6.71 (br s, 1H), 6.68 (wd, 1H), 6.10 (w t, 1H), 5.98 (wt, 1H), 5.12 (br s, 1H), 4.78 (td, 1H), 4.51 (td, 1H), 4.29 (m, 1H), 4.30-3.99 (m, 2H), 3.97 (dd, 1H), 3.85 (dd, 1H), 3.21 (d, 1H), 3.10 (dd, 1H), 2.86 (d, 1H), 2.81 (dd, 1H), 1.45 (s, 3H).

Provenance & Evidence