Benzoic Acid → 5-[4-(4-(2-t-Butoxycarbonylamino-2-methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione

HRID 1007284Notes

Reaction equation

HRID 1007284 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])CC1C=CC=CC=1OC1C=CC(C=O)=CC=1.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[S:37]1[CH2:41][C:40](=[O:42])[NH:39][C:38]1=[O:43].[C:44](O)(=O)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.N1CCCCC1.[OH2:59]>>[C:25]([O:24][C:22]([NH:21][CH:4]([C:3]([O:2][CH3:1])=[O:29])[CH2:36][C:30]1[CH:35]=[CH:34][C:33]([O:59][C:48]2[CH:49]=[CH:50][C:45]([CH:44]=[C:41]3[S:37][C:38](=[O:43])[NH:39][C:40]3=[O:42])=[CH:46][CH:47]=2)=[CH:32][CH:31]=1)=[O:23])([CH3:27])([CH3:28])[CH3:26]

Participants

7

Reactant 6

HCID 243Benzoic AcidHCID 962WaterHCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 22669057Methyl-2-[(t-butoxycarbonyl)amino]-3-[-(4-formylphenoxy) phenyl]propanoate

Product 1

HCID 765731105-[4-(4-(2-t-Butoxycarbonylamino-2-methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dioneYield 96%

Procedure

To a solution of methyl-2-[(t-butoxycarbonyl)amino]-3-[-(4-formylphenoxy)phenyl]propanoate obtained in step (i) above in anhydrous toluene (10 g, 25 mmol), 2,4-thiazolidinedione (3.53 g, 30 mmol) was added followed by benzoic acid (0.46 g, 3.75 mmol) and piperidine (0.28 g, 3.25 mmol). The solution was heated to reflux at 145-155° C. with continuous removal of water using Dean-Stark apparatus for 5 hr. The solution was cooled to RT and the yellow solid was precipitated to afford the title compound (yield 11.9 g, 96%, purity 96.5% by HPLC, mp: 160-164° C.).

Workup

  1. temperatureThe solution was heated
  2. customthe yellow solid was precipitated

Sources & evidence

ORD record
ord-7afe3d99db4f4703bdeb36d3f0dea69f
Source dataset
uspto-grants-2004_09
Patent number
US06794401B2

Reaction notes

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