Water → HCID 18973443, compound

HRID 2394393Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2.00 g of 5-[1-(4-methoxycarbonylbenzyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 9 and 0.43 g of lithium hydroxide monohydrate, there were, in order, added 40 ml of tetrahydrofuran, 40 ml of water and 20 ml of methanol and the resulting mixture was stirred at 60° C. for 2 hours. After concentrating the reaction solution to about 40 ml, the concentrate was neutralized with a 10% citric acid aqueous solution, followed by extraction with dichloromethane (100 ml×3). The extract was washed with a saturated common salt solution, dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to give 1.54 g of 5-[1-(4-carbonylbenzyl)indol-4-yl]methyl-2,4-thiazolidinedione as pale yellow crystals. The yield thereof was found to be 80%.

Workup

concentrationAfter concentrating the reaction solution to about 40 ml
extractionfollowed by extraction with dichloromethane (100 ml×3)
washThe extract was washed with a saturated common salt solution
dry with materialdried over anhydrous sodium sulfate
customfollowed by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-4ee0b59dc84946579ad6d321b0081712
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811439

Reaction notes

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