Thiazolidinedione → Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)-2'-methylbiphenyl-3-ylmethyl]-n-methylcarbamate

HRID 585004Notes

Reaction equation

HRID 585004 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=2)=[C:5]([CH3:25])[CH:4]=1)=O.[S:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32]>>[O:32]=[C:27]1[NH:28][C:29](=[O:31])[C:30](=[CH:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])[CH:10]=3)=[C:5]([CH3:25])[CH:4]=2)[S:26]1

Participants

3

Reactant 2

HCID 5437ThiazolidinedioneHCID 90739199Tert-butyl (4'-formyl-2'-methylbiphenyl-3-ylmethyl)-n-methylcarbamate

Product 1

HCID 90741827Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)-2'-methylbiphenyl-3-ylmethyl]-n-methylcarbamate

Procedure

In a manner similar to that of Example 1(f), by reacting 3.95 g (11.6 mmol) of tert-butyl (4′-formyl-2′-methylbiphenyl-3-ylmethyl)-N-methylcarbamate with 1.4 g (11.6 mmol) of 2,4-thiazolidine dione, and after purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (8/2), 3 g (59%) of the expected product are obtained in the form of a yellow solid with a melting point of 156° C.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a heptane/ethyl acetate mixture (8/2), 3 g (59%) of the expected product
  3. customare obtained in the form of a yellow solid with a melting point of 156° C.

Sources & evidence

ORD record
ord-218e2f82c5f74423a49da6ef2b066857
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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