Reaktion #7447

Reaktionsgleichung

Water

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

2-t-butoxycarbonylaminopropionic acid

N,N′-Dicyclohexylcarbodiimide

→

title compound

Ausbeute 23.0%

5-[4-(4-(2-(2-t-Butoxycarbonylaminopropanamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione

Ausbeute 23.0%

Lösungsmittel

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 15 minutes
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for another 15 minutes
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed with water (100 ml)
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated

Vorschrift

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione hydrochloride (2.3 g, 5.27 mmol) and 2-t-butoxycarbonylaminopropionic acid (0.997 g, 5.27 mmol) in tetrahydrofuran (20 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (1.086 g, 5.27 mmol) was added to this solution and stirring was continued for 1.5 h at ambient temperature. Water (200 ml) was added to the reaction mixture, stirred for 15 minutes, ethyl acetate (250 ml) was added and stirring was continued for another 15 minutes. The organic layer was separated and washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, which was purified by column chromatography (0.7 g, yield 23%).

Quelle