Troglitazone → t-Butyl alpha-{5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidin-3-yl}acetate

HRID 1030382Notes

Reaction equation

HRID 1030382 reaction equation
[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>CC(C)=O>[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[N:24]([CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 5591TroglitazoneHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 19822185t-Butyl alpha-{5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidin-3-yl}acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure described in Example 44, 1 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione [prepared as described in Example 27(b)], 0.47 g of anhydrous potassium carbonate, 0.93 g of t-butyl bromoacetate and 8 ml of acetone gave the title compound.

Sources & evidence

ORD record
ord-85e83aa784684da7990e25ca7fa649d3
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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