Triethylamine → ethyl 6-[[3-[(5-methoxy-5-oxopentanoyl)amino]-5-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoate

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Reaction Steps

4-Chlorocarbonyl-butyric acid methyl ester (20.4 μL, 0.148 mmol) was added to a solution of 6-(3-{2-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-4-yl}-ureido)-hexanoic acid ethyl ester (70.8 mg, 96.4 μmol, Example 278: step c) and triethylamine (41.2 μL, 0.296 mmol) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight at rt, then diluted in EtOAc, washed with water and brine, and dried over magnesium sulfate. Removal of solvents in vacuo followed by flash chromatography (75–100% EtOAc/hexanes) yielded the title compound as a brown oil (45.5 mg, 54.5%). ESI-MS (m/z): Calcd. for C39H51N5O10S3: 846.3 (M+1); found: 845.9.

Provenance & Evidence