Hydrochloric Acid → HCID 58975136, compound

Reaction equation

C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[CH:22]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:27])=[O:2])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH:14]=2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

Procedure

In a 12 L RBF, charge 4-(3-cyclopentyl-indole-1-sulfonyl)-benzoic acid methyl ester (465 g 1.213 mol) and THF (4.7 L). Add 5N NaOH (485 ml) dropwise at ambient temperature. Stir the solution at room temperature overnight. Bring the pH of the reaction to 1 with c.HCl. Separate the layers and extract the aqueous layer with ethyl acetate (4 L). Dry the combined organic layers over sodium sulfate, filter and rinse with ethyl acetate. Concentrate the organics under vacuum to give an off-white solid (401 g, yield=89.5%) of the title compound.