1,2-Dichloroethane → 1-(4-(2-(1-Methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl)-phenyl)-4(S)-hydroxy-2-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino)-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane

Participants

Reaction Steps

With the exclusion of air, 128 mg (0.67 mmol) of N-methoxycarbonyl-(L)-tert-leucine (Example 2e), 243 mg (1.27 mmol) of EDC and 114 mg (0.84 mmol) of HOBT are dissolved in 2 ml of DMF. After 15 min, 0.35 ml (2.5 mmol) of TEA and 286 mg (0.42 mmol) of 1-{4-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-phenyl}-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane hydrochloride in 1.5 ml of DMF are added. After 20 hours, the mixture is worked up as described under Example 25. Chromatography (SiO2 ; ethyl acetate/toluene/methylene chloride 2:1:1) yields the title compound: TLC: Rf =0.22 (methylene chloride/ethyl acetate 1:1); HPLC20-100 : tRet =17.3; FAB MS (M+H)+ =814.

Provenance & Evidence