Acetic Acid → 5-(4-Methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione

HRID 1275066Notes

Reaction equation

C(O)(=O)C.O.[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:44]=[CH:43][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:18]2=[O:42])=[CH:14][CH:13]=1)=[O:9]>O1CCOCC1>[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:42])=[CH:43][CH:44]=1)=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

1700 ml of acetic acid and then 400 ml of water were added at room temperature to a suspension of 344 g of 5-(4-methoxycarbonylmethoxybenzyl)-3-triphenylmethyl-thiazolidine-2,4-dione [prepared as described in step (f) above] in 400 ml of 1,4-dioxane and the resulting mixture was stirred for 5 hours at 80° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane, a 2:1 by volume mixture of ethyl acetate and hexane and then ethyl acetate as eluents, to give 161.7 g of the title compound, melting at 100-106° C.

Workup

customAt the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure
customthe resulting residue was purified by column chromatography through silica gel using a 1:2
additionby volume mixture of ethyl acetate and hexane
additiona 2:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-cf104ad2f4104ece9439c2e922c1429a
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159997

Reaction notes

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