Hydrochloric Acid → HCID 131731129, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl glycinate hydrochloride (944 mg) in DMF (6.0 mL) was stirred for 5 min. p-Iodobenzyl bromide (2.00 g) was added. The heterogeneous system was warmed to 50° C. and stirred for 5 min, during which time, most solids dissolved. K2CO3 (2.80 g, granular) was added steadily over 5 min. After 2 h, the reaction was cooled to 23° C. Conc. aq. HCl (3.3 mL) was added, followed by H2O (7.0 mL). The heterogeneous mix was stirred for 15 min and filtered (the cake was washed with CH3CN (4×5 mL)). The net filtrate was concentrated until no CH3CN remained. The crude product solution was filtered through a 0.45 micron Teflon filter and loaded directly onto a Teledyne Isco ‘gold’ 100 gram column and flashed (Eluent: 0.05% w/v aq. HCl/CH3CN 95:5→0:100), giving DK (688 mg, 29% yield) as an HCl salt. 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.78 (s, 2H), 7.84 (d, J=7.8 Hz, 2H), 7.36 (d, J=7.8 Hz, 2H), 4.23 (q, J=7.0 Hz, 2H), 4.15 (s, 2H), 3.95 (s, 2H), 1.25 (t, J=7.0 Hz, 3H). LCMS-ESI+: calc'd for C11H16INO2: 320.0 (M+H+). Found: 319.9 (M+H+).

Provenance & Evidence