反応 #11702

反応方程式

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

isobutylchloroformate

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

4-methyl morpholine

→

title compound

収率 69.7%

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

収率 69.7%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at ambient temperature
2. 2
   ろ過The reaction mixture was filtered through a pad of celite
3. 3
   洗浄the filter cake was washed with ethyl acetate
4. 4
   濃縮The filtrate was concentrated in vacuo
5. 5
   workup.ADDITIONdiluted with ethyl acetate
6. 6
   洗浄washed with water and brine
7. 7
   乾燥The organic layer was dried over magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo

実験手順

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).

出典