Toluene → (S)-Methyl 3-methyl-2-(N-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)butanoate

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반응 단계

N-[[2′-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]-L-valine methyl ester oxalate (150 g, 0.215 mole) was added to the mixture of toluene (450 ml) and DM water (300 ml), and basified with 10% w/w aqueous sodium bicarbonate solution (450 ml) at 20-30° C. The organic layer was separated and washed successively with DM water (150 ml) followed by saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and reacted with valeryl chloride (33.7 g) in the presence of N,N-Diisopropylethylamine (55.6 g) at 0-5° C. The reaction mixture was stirred for 3 h at 5-10° C. and washed with DM water (150 ml), 10% w/w sodium carbonate solution (68 ml) followed by 10% w/w aqueous oxalic acid solution (40 ml). The organic phase was concentrated completely under reduced pressure to dryness to yield N-[[2′-(1-triphenylmethyltetrazol-5-yl]biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester as oily mass (141.3 g)

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