Réaction #7445

Équation de réaction

Water

5[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride

N-Boc-pyrolidin-2-carboxylic acid

N,N′-Dicyclohexylcarbodiimide

→

required product

Rendement 32.4%

2-(2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-1-methoxycarbonylethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Rendement 32.4%

Solvants

dimethyl formamide

Ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 15 minutes
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for another 15 minutes
4. 4
   AutreThe organic layer was separated
5. 5
   Lavagewashed with water (75 ml)
6. 6
   Séchagedried over anhydrous sodium sulphate
7. 7
   Concentrationconcentrated
8. 8
   Autreto afford the crude product, which
9. 9
   Autrewas purified by column chromatography

Mode opératoire

A solution of 5[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (2.5 g, 5.76 mmol) and N-Boc-pyrolidin-2-carboxylic acid (1.238 g, 5.76 mmol) in dimethyl formamide (25 ml) was stirred for 60 minutes at 0° C. N,N′-Dicyclohexylcarbodiimide (1.423 g, 6.91 mmol) was added to it and stirring was continued for 10 h at ambient temperature. Water (200 ml) was added to the reaction mixture and stirred for 15 minutes. Ethyl acetate (200 ml) was added to the reaction mixture and stirring continued for another 15 minutes. The organic layer was separated, washed with water (75 ml), dried over anhydrous sodium sulphate and concentrated to afford the crude product, which was purified by column chromatography to furnish the required product (1.1 g, yield 32.4%).

Source