Hydrochloric Acid → HCID 59118247, compound

Participants

Reaction Conditions

Reaction Steps

To 670 mg (1.25 mmol) of crude 3-{[(2R)-2-({(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]sulfanyl}benzoic acid (Example 173) diluted in 5 mL 1,4-dioxane, was added 0.5 mL of 6N hydrochloric acid slowly. The resulting mixture was stirred at 45° C. for 2 hours. After this time the mixture was concentrated in vacuo, dissolved in 2 mL of 1:1 methanol to water, and purified by HPLC (0-70% acetonitrile/0.1% TFA) to afford 28.5 mg (5% yield) of the desired product as the bis TFA salt. MH+ 437.3. 1H NMR (CDCl3, δ): 8.91 (br. S, 1H), 8.63 (d, 1H), 8.56 (dd, 1H), 7.89 (m, 1H), 7.72 (dt, 1H), 7.62 (m, 1H), 7.49 (m, 1H), 7.39 (m, 1H), 7.31 (m, 1H), 7.27 (m, 1H), 7.24 (dd, 1H), 6.90 (d, 1H), 6.35 (br. S, 1H), 5.07 (m, 1H), 4.48 (m, 1H), 3.32 (m, 4H), 3.16 (m, 1H), 2.78 (m, 2H), 2.04 (m, 1H), 1.71 (m, 1H).

Provenance & Evidence