Hydrochloric Acid → HCID 10219783, compound

Reaction equation

[C:1]([NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13]C(=O)C)([CH3:4])([CH3:3])[CH3:2].O.Cl>C1COCC1>[C:1]([NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])([CH3:4])([CH3:2])[CH3:3]

Participants

Procedure

The product from Step A (2.35 g, 0.010 mol) was dissolved in THF wand 10 mL of water was added to form a clear suspension. Hydrochloric acid (5%) was added until the solution reached a pH˜1. The reaction mixture was then refluxed for 24 hours. TLC indicated that about half of the starting material remained, so an additonal 10 mL of 5% hydrochloric acid was added and the reaction mixture was refluxed for 24 hours. The THF was then removed by rotoevaporation and the remaining aqueous mixture was extracted with hexanes (2×20 mL). The combined hexane layers were washed with water (2×40 mL), dried over MgSO4 and the hexane removed in vacuo to provide 1.56 g (80.8% yield) of the title compound as a white crystalline solid, m.p. 78-79.5° C.