Imidazole → HCID 22874307, compound

Participants

Reaction Steps

Analogously to Example 1 j), 1.06 g of 5(S)-(Boc-amino)-4(S)-hydroxy-6-(p-fluorophenyl)-2(R)-(p-trifluoromethylphenylmethyl)-hexanoic acid in 2.3 ml of DMF are silylated with 1.47 g of tert-butyldimethylchlorosilane and 1.18 g of imidazole. Hydrolysis of the silyl ester function with 1.76 g of potassium carbonate in 50 ml of methanol/THF/water 3:1:1 yields, after column chromatography (SiO2, hexane/ethyl acetate 2: 1), the title compound: TLC Rf (D)=0.15; 1H-NMR (200 MHz, CD3OD): 7.59 and 7.39 (2d, 8 Hz, per 2 H), 7.19 and 6.98 (2 m, per 2 H), 6.47 and 5.90 (d, approximately 9 Hz, together 1 H), 3.9-3.65 (m, 2 H), 3.15-2.8 (m, 4 H), 2.53-2.37, 2.07-1.9 and 1.6-1.4 (3 m, per 1 H), 1.37-1.22 (m, 9 H), 0.94 (s, 9 H), 0.2-0.1 (m, 6 H).

Provenance & Evidence