HCID 69286564, compound → HCID 11192300, compound

Participants

Reaction Steps

A solution of {(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester (110 mg, 0.18 mmol, see procedure 12c) in THF (4 mL) was charged with trichloroacetylchloride (0.063 mL, 0.53 mmol). The reaction was stirred for 12 h at RT and concentrated in vacuo. The residue was dissolved in THF (4 mL). The resultant solution was charged with ethylamine (0.175 mL of a 2.0 M solution in THF, 0.35 mmol). The reaction was stirred for 4 h at RT and concentrated in vacuo. The residue was dissolved in EtOAc and washed successively with water and brine. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via flash chromatography to afford (2,4-dimethyl-benzyl)-[(2S,3S)-2-{2-[3-(3-ethyl-ureido)-5-trifluoromethyl-phenylcarbamoyl]-acetylamino}-3-hydroxy-hexyl]-carbamic acid benzyl ester as an oil (55 mg, 45% yield). MS found: (M+Na)+=722.4. (16b) The compound (2,4-dimethyl-benzyl)-[(2S,3S)-2-{2-[3-(3-ethyl-ureido)-5-trifluoromethyl-phenylcarbamoyl]-acetylamino}-3-hydroxy-hexyl]-carbamic acid benzyl ester was dissolved in MeOH (2 mL). This solution was charged with 5% Pd/C, Degussa style (11 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. Purification of the residue by reverse-phase HPLC provided the title compound as a white powder after lyopholization. MS found: (M+H)+=566.3.

Provenance & Evidence