Hydrochloric Acid → {2-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic Acid

HRID 660804Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of {2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic acid methyl ester in water/MeOH/MeCN (1:1:1) is added KOH and the mixture is heated at 60° C. for 1 h. The mixture is cooled to RT and is acidified with 1N HCl. The mixture is purified by preparative HPLC to give the title compound. (M−1)−=375. HPLC retention time=0.63 min (Method A).

Workup

temperatureThe mixture is cooled to RT
customThe mixture is purified by preparative HPLC

Sources & evidence

ORD record: ord-f3a9c62cb204450b9ce723c79575eaf4
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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