反应详情

At 0° C. to a solution of (S,E)-3-hydroxy-1-((R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-(tritylthio)hept-4-en-1-one (934 mg, 1.66 mmol, prepared according to the procedure in Yurek-George, A. et al, J. Am. Chem. Soc. 2004, 126, 1030) in THF (30 mL) was added a solution of LiOH (196.1 mg, 8.19 mmol) in H2O (10 mL). The reaction mixture was allowed to warm to rt over 1 h, whereupon 1M HCl was added until the pH reached 2. EtOAc (30 mL) was then added and the layers were separated. The aqueous layer was extracted with EtOAc (20 mL) the organic layers were combined, dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography (eluant 3:7-1:1-1:0 EtOAc/Hexane) gave the 6 as a white solid (600 mg, 1.43 mmol, 86%).

1. additionwas added until the pH
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with EtOAc (20 mL) the organic layers
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customPurification by flash column chromatography (eluant 3:7-1:1-1:0 EtOAc/Hexane)