Dimethylformamide → HCID 178455998, compound

Participants

Reaction Steps

109 mg (0.38 mmol) of 3-(RS)-(1-naphthylmethyl)succinic acid 1-ethyl ester were dissolved in 6 ml of acetonitrile and 1 ml of dimethylformamide and, after the addition of 135 mg (0.35 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide, 39 mg (0.38 mmol) of triethylamine and 144 mg (0.38 mmol) of HBTU, stirred at room temperature for 6 hours. Subsequently, the reaction solution was evaporated in a high vacuum and the residue was dissolved in 50 ml of ethyl acetate and washed 3 times with 10 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated under reduced pressure, and the residue was chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which contained 0.1% ammonium hydroxide, to obtain 103 mg (45%) of (RS)-β-[[(S)-1-[[(1S,2S, 4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]-1-naphthylbutyric acid ethyl ester as a yellowish foam. MS: 594 (M-ethanol-water)+

Provenance & Evidence