Water → HCID 68775729, compound

HRID 2262977Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:24][N:23]=[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1)(=O)C.[OH-].[Na+].O>CO.O1CCCC1>[OH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:24][N:23]=[C:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3-({[4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazin-1-yl]carbonyl}amino)phenyl acetate (635 mg, 1.50 mmol) in methanol/tetrahydrofuran (2:1) (60 ml) was added an aqueous 1 N sodium hydroxide solution (1.5 ml), and the mixture was stirred at 70° C. for 3 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 360 mg (62.9%) of the desired product as a solid.

Workup

extractionthe resulting solution was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-f887509590994d1e8a3334f1a6729c7a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

Loading…