반응 #91994

반응 방정식

(S)-3-[4-aminophenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

2,6-dichlorobenzoyl chloride

DIPEA

→

(S)-2-tert-butoxycarbonylamino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester

수율 88.5%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타to afford a white suspension at this time TLC analysis of the mixture
2. 2
   여과Then, the solids were collected by filtration
3. 3
   세척the solids were washed with dichloromethane (150 mL) and air
4. 4
   기타dried

실험 절차

To a solution of (S)-3-[4-aminophenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (37.57 g, 127.6 mmol) and 2,6-dichlorobenzoyl chloride (29.45 g, 140.6 mmol) in dichloromethane (350 mL) was added DIPEA (24.8 g, 192 mmol) at room temperature. The brown solution was stirred for 15 h at room temperature to afford a white suspension at this time TLC analysis of the mixture indicated the absence of starting material. Then, the solids were collected by filtration and the solids were washed with dichloromethane (150 mL) and air dried to obtain 52.75 g (88.4% yield) of (S)-2-tert-butoxycarbonylamino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester as a white solid: mp 192-194° C. ES(+)-HRMS m/e calcd. for C22H24Cl2N2O5 (M+H)+ 466.1062, obsd. 466.1069.

출처