반응 #7445

반응 방정식

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

수율 32.4%

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

수율 32.4%

용매

dimethyl formamide

Ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 15 minutes
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for another 15 minutes
4. 4
   기타The organic layer was separated
5. 5
   세척washed with water (75 ml)
6. 6
   건조dried over anhydrous sodium sulphate
7. 7
   농축concentrated
8. 8
   기타to afford the crude product, which
9. 9
   기타was purified by column chromatography

실험 절차

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%).

출처