Hydrochloric Acid → HCID 58746551, compound

Participants

Reaction Conditions

Reaction Steps

Methyl (2S)-2-amino-3-[3-chloro-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-phenyl]-propanoate trifluoroacetate (145 mg, 0.314 mmol) was dissolved in trifluoroacetic acid (3 mL) and heated in the microwave at 130° C. for 180 s. The reaction was concentrated in vacuo and azetroped with toluene (5 mL). The product was dissolved in methanol (2 mL), was treated with triethylamine (170 μL, 1.2 mmol) and then benzenesulfonyl chloride (60 μL, 0.47 mmol). The solution stirred at rt for 1 h. 4 M aqueous lithium hydroxide solution (0.782 mL) was added and the solution stirred 3 h at rt. The solution was acidified with aqueous hydrochloric acid solution (1.0 N, 4.0 mL), diluted with methanol to 10 mL volume, and then purified by reverse phase HPLC to afford product as a white solid (108 mg, 73%). 1H NMR (400 MHz, CD3OD): δ 7.66–7.64 (m, 2H), 7.63–7.51 (m, 1H), 7.44–7.38 (m, 3H), 7.31–7.16 (m, 2H), 5.65–5.61 (m, 1H), 4.10–4.03 (m, 1H), 3.48–3.42 (m, 1H), 3.29–3.27 (m, 1H), 3.12–3.07 (m, 1H), 2.88–2.81 (m, 1H); LCMS found for C18H21ClN3O7S2 (M+H)+: m/z=490.

Provenance & Evidence