N-Methyl-D-glucamine → HCID 25168154, compound

Participants

Reaction Steps

To a solution of 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid (Ex. 4, 0.60 g, 1.18 mmol) in THF (2.0 mL) was added a solution of N-methyl-D-glucamine (meglumine, 0.23 g, 1.18 mmol) in water:THF (1:1, 2.0 mL). The resulting solution was stirred at room temperature for 30 min, then concentrated under reduced pressure and the solid residue was triturated with THF (2.0 mL×2). The material was then taken up in Ethyl acetate/hexanes and the resulting slurry was stirred at room temperature overnight. The solid was collected on filter paper and dried in vacuo to afford 0.68 g (82%) of the title compound as a white solid, mp 179-182° C. 1H-NMR (400 MHz, DMSO-d6): δ 7.27 (s, 1H), 7.10 (s, 2H), 6.57 (s, 1H), 5.73 (brs, 2H), 4.66 (brs, 3H), 3.88 (s, 3H), 3.83-3.85 (m, 2H), 3.66-3.67 (m, 2H), 3.57-3.61 (m, 2H), 3.47-3.49 (m, 1H), 3.40-3.44 (m, 1H), 2.92-2.98 (m, 3H), 2.82-2.87 (m, 1H), 2.47 (s, 3H), 2.33-2.38 (m, 2H), 1.90-1.93 (m, 2H), 1.43-1.50 (m, 2H), 1.35 (s, 18H). HRMS (ESI) Calcd. for C32H53N3O10S2, 704.3250 ([M+H]+). Found: 704.3269. Anal. Calcd. for C32H53N3O10S2. 1/2H2O: C, 54.60; H, 7.59; N, 5.97; S, 9.11. Found: C, 54.29; H, 7.45; N, 5.97; S, 8.85.

Provenance & Evidence