Trifluoroacetic acid → R-Lotrafiban

Participants

Reaction Steps

Using the procedure of Preparation 8(j), except substituting the compounds of Example 26(b) and 27(b) for the compound of Preparation 8(i) gave the following compounds: 26(c). (R)-7-[(4,4'-bipiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate: [α]D +92.4 (c 0.5,CH3OH); MS(ES) m/e 429 [M+H]+ ; 427 [M-H]- ; HPLC tR 12.7 min (Ultrasphere C18, 4.6×250 mm, 1.5 mL/min, gradient, A:acetonitrile B: water-0.1% TFA, 5-60% acetonitrile over 20 min, UV detection at 220 nm); Anal. (C23H32N4O4.4.5 CF3CO2H.3.33 H2O) calcd: C, 37.44; H, 4.16; N, 5.29. found: C, 37.43; H, 3.81; N, 5.20. 27(c). (S)-7-[(4,4'-bipiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate: [α]D -105.9 (c 0.6,CH3OH); MS(ES) m/e 429 [M+H]+ ; 427 [M-H]- ; HPLC tR 12.6 min (Ultrasphere C18, 4.6×250 mm, 1.5 mL/min, gradient, A:acetonitrile B: water-0.1% TFA, 5-60% acetonitrile over 20 min, UV detection at 220 nm); Anal. (C23H32N4O4.3 CF3CO2H.1.25 H2O) calcd: C, 43.92; H, 4.77; N, 7.06. found: C, 44.09; H, 5.00; N, 7.29.

Provenance & Evidence