Potassium Carbonate → HCID 44625098, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N′-[4-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-fluoro-6-((S)-3,3,3-trifluoro-2-hydroxy-propyl)-phenyl]-N,N-dimethyl-formamidine (0.1 g, 0.16 mmol) in anhydrous THF was added KOSi(CH3)4 (0.11 g, 0.8 mmol) and the reaction mixture was heated for 16 h at 60° C. The reaction mixture was added to cold 10% aq. K2CO3 solution and extracted with EtOAc. The combined organic layers were washed with 10% aq. K2CO3 solution and brine, dried over MgSO4, filtered and evaporated. The residue was converted into the hydrochloride salt with 1N HCl in Et2O and the precipitated salt was dried under reduced pressure to yield the title compound as a light yellow solid: TLC (CH2Cl2-MeOH-AcOH-H2O 180:20:2:1) Rf=0.46; HPLC RtA=1.79 min; ESIMS [M+H]+=547; HPLC RtA=1.22 min; ESIMS [M+H]+=337; 1H NMR (400 MHz, CDCl3+1% D2O): δ 7.34 (m, 3H), 7.12 (d, 1H), 6.79 (dd, 1H), 6.66 (s, 1H), 4.14 (m, 1H), 3.87 (dd, 1H), 3.74 (dd, 1H), 3.38 (dt, 1H), 2.8-3.2 (m, 6H), 2.72 (dd, 1H), 2.63 (t, 1H), 2.55 (dd, 1H), 2.29 (m, 1H), 1.34 (s, 9H).

Provenance & Evidence