반응 #11702

반응 방정식

(S)-2-(4-fluoro-benzylamino)-propionic acid methyl ester

isobutylchloroformate

(R)-2-tert-butoxycarbonylamino-propionic acid

4-methyl morpholine

→

title compound

수율 69.7%

(2S)-2-[(2R)-(2-tert-Butoxycarbonylamino-propionyl)-(4-fluoro-benzyl)-amino]-propionic acid methyl ester

수율 69.7%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at ambient temperature
2. 2
   여과The reaction mixture was filtered through a pad of celite
3. 3
   세척the filter cake was washed with ethyl acetate
4. 4
   농축The filtrate was concentrated in vacuo
5. 5
   workup.ADDITIONdiluted with ethyl acetate
6. 6
   세척washed with water and brine
7. 7
   건조The organic layer was dried over magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo

실험 절차

To a solution of (R)-2-tert-butoxycarbonylamino-propionic acid (37 g, 195 mmol) in dry tetrahydrofuran (250 mL) at 0° C. was added 4-methyl morpholine (21.5 mL, 195 mmol) followed by isobutylchloroformate (25.3 mL, 195 mmol). The reaction was allowed to warm to ambient temperature and stirred for two hours. This was followed by the addition of (S)-2-(4-fluoro-benzylamino)-propionic acid methyl ester (34.4 g, 162 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction mixture was filtered through a pad of celite and the filter cake was washed with ethyl acetate. The filtrate was concentrated in vacuo, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (43.2 g).

출처