Sodium Hydroxide → (R)-2-Hydroxy-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidin-1-yl}-propan-1-one

Participants

Reaction Steps

Following the procedure for 318, 9-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and sodium D-lactate in DMF were reacted. After purification by flash chromatography a lactate-ester by-product of the title compound was present. The mixture (0.11 g, 0.2 mmol) was dissolved in 1,4-dioxan (2 mL) and treated with 1M aqueous sodium hydroxide solution (0.2 mL, 0.2 mmol). The reaction mixture was stirred for 2 hours then diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (×2) and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Further drying under vacuum gave 398 (90 mg, 36%). LCMS: RT=10.71 min, [M+H]+=440. 1H NMR δ (ppm) (CDCl3): 8.37 (1H, s), 7.90 (1H, s), 7.20-7.12 (1H, m), 7.06 (1H, dd, J=8.28, 5.28 Hz), 5.85-5.76 (1H, m), 4.64-4.30 (4H, m), 4.25-4.10 (3H, m), 3.98-3.87 (1H, m), 3.45-3.35 (2H, m), 1.62 (6H, d, J=6.65 Hz), 1.33 (3H, dd, J=11.04, 6.67 Hz). 1 Exchangeable not observed

Provenance & Evidence