Water → HCID 10283127, compound

Reaction equation

C[O:2][C:3](=[O:42])[CH:4]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][NH:24][C:25]([C:27]3[O:28][C:29]([O:32][C:33]4[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=4)=[CH:30][CH:31]=3)=[O:26])[CH:19]=2)[C:14]=1[Br:41])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].O>CO>[Br:41][C:14]1[C:15]2[C:20](=[CH:19][C:18]([CH2:23][NH:24][C:25]([C:27]3[O:28][C:29]([O:32][C:33]4[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=4)=[CH:30][CH:31]=3)=[O:26])=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:42])=[O:2]

Participants

Procedure

A mixture of 2-[1-bromo-6-({[5-(3,5-dichloro-phenoxy)-furan-2-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-3-phenyl-propionic acid methyl ester (0.34 g, 0.508 mmol), prepared in the previous step, 1N NaOH (1.50 mL, 1.5 mmol), 5 mL of water and 50 mL of methanol was stirred under nitrogen at room temperature for 18 h (overnight). The methanol was removed under reduced pressure. The solid that formed was collected by filtration and identified as the sodium salt salt of 2-[1-bromo-6-({[5-(3,5-dichloro-phenoxy)-furan-2-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-3-phenyl-propionic acid (0.1537 g, 46%). The clear filtrate was acidified with 1N HCl. The solid that precipitated was collected by filtration and dried under reduced pressure to give the title compound (0.0905 g, 27%) as a white solid, mp 86-100° C.