4-Methylmorpholine → (2S)-2-[(2R)-(2-Tert-Butoxycarbonylamino-Propionyl)-(4-Fluoro-Benzyl)-Amino]propionic Acid Methyl Ester

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).

1. stirringThe resulting mixture was stirred overnight at ambient temperature
2. filtrationThe reaction mixture was filtered through a pad of celite
3. washthe filter cake was washed with ethyl acetate
4. concentrationThe filtrate was concentrated in vacuo
5. additiondiluted with ethyl acetate
6. washwashed with water and brine
7. dry with materialThe organic layer was dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORDレコード

ord-c3814d07017d476faad65d26565c6cf8

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07098212B2