1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(2,2-dimethoxyethyl)-2-(4-methylbenzenesulfonamido)pent-4-ynamide

Participants

Reaction Steps

A mixture of (R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid (11.0 g, 41.2 mmol), HOBt (6.67 g, 49.4 mmol), iPr2NEt (6.40 g, 49.4 mmol), (2,2-dimethoxyethyl)amine (8.70 g, 82.33 mmol), and EDCI (9.5 g, 49 mmol) in DMF (100 mL) was stirred for 24 h at RT. The reaction mixture was concentrated, taken up in H2O, and extracted with EtOAc (3×). The organic extracts were dried over MgSO4 and concentrated to give the title compound. 1H NMR (400 MHz, CDCl3): δ 2.15 (s, 1H), 2.43 (m, 1H), 2.51 (s, 3H), 2.88 (m, 1H), 2.94 (s, 3H), 2.96 (s, 3H), 3.37 (m, 3H), 3.85 (m, 1H), 4.33 (m, 1H), 6.78 (s, 1H), 7.33 (d, 8.0 Hz, 2H), 7.76 (d, 8.0 Hz, 2H), 8.01 (s, 1H).

Provenance & Evidence