Hydrochloric Acid → HCID 57110839, compound

Participants

Reaction Steps

The (2S)-2-amino-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoic acid was dissolved in dioxane:water (1:1) (40 mL). Triethylamine (5.1 mL, 50.4 mmol) was added to the solution followed by 2-butynyloxybenzenesulfonyl chloride (4.1 g, 16.8 mmol). The resulting mixture was stirred for 15 h at room temperature. The mixture was acidified to pH˜2 with 1N hydrochloric acid and partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate. Removal of the solvent gave 5.78 g (83%) of (2S)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoic acid as a solid; 1H NMR (300 MHz, acetone-d6) δ 1.34 (s, 3H), 1.39 (s, 3H), 1.66 (m, 2H), 2.06 (m, 3H), 2.54-2.68 (m, 2H), 3.89 (m, 1H), 4.82 (m, 2H), 6.56 (d, 1H, J=9.0 Hz), 7.12 (d, 2H, J=8.7 Hz), 7.81 (d, 2H, J=8.7 Hz). HRMS (C18H25NOS2)(M+H); calcd. 416.1196, found 416.1199.

Provenance & Evidence