(R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid → (R)-3-(1-((R)-6-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)-2-(4-methylbenzenesulfonamido)propanoic acid

Participants

Reaction Steps

A solution of (R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid (6.25 g, 23.4 mmol) and (R)-methyl 5-azido-5,6,7,8-tetrahydronaphthalene-2-carboxylate (5.4 g, 23.4 mmol) in 80 mL t-BuOH was treated with sodium ascorbate (0.47 g, 2.34 mmole in 24 mL H2O) and CuSO4.5H2O (0.58 g, 2.34 mmol in 24 mL H2O). An additional portion of H2O (50 mL) was then added to the reaction mixture. After stirring for 48 h at RT, the reaction mixture was diluted with H2O. A precipitate had formed that was filtered and air-dried. MS (m/z): 499.4 (m+H).

Provenance & Evidence