تفاعل #220741

معادلة التفاعل

NaOH

Triethylamine

2-(tert-butoxycarbonylamino)-5-(trifluoromethyl)benzoic acid

EDCI

HOBt

(R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine

→

(R)-3-[[N-[2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl]glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   استخلاصthe resulting mixture was extracted with dichloromethane
3. 3
   استخلاصThe obtained extract
4. 4
   تجفيفwas dried over anhydrous Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىpurified by column chromatography [SiO2, hexane/ethyl acetate=(1:1) to (1:4)] to thereby afford (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine (9.41 g, 91%) as a white amorphous solid

الإجراء التجريبي

Triethylamine (2.9 mL, 20.5 mmol), 2-(tert-butoxycarbonylamino)-5-(trifluoromethyl)benzoic acid (6.27 g, 20.5 mmol), EDCI (3.9 g, 20.5 mmol) and HOBt (2.8 g, 20.5 mmol) were added to a dichloromethane (100 mL) solution of (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine (5.0 g, 18.7 mmol). The resulting reaction mixture was stirred at room temperature overnight. A 2 M aqueous solution (80 mL) of NaOH was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The obtained extract was dried over anhydrous Na2SO4, filtered, concentrated and purified by column chromatography [SiO2, hexane/ethyl acetate=(1:1) to (1:4)] to thereby afford (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine (9.41 g, 91%) as a white amorphous solid. ESI/MS m/e 555.2 (M++H, C26H30ClF3N4O4).

المصدر