Methyl (S)-2-benzyloxycarbonylamino-3-chlorocarbonylpropionate → Methyl (S)-2-benzyloxycarbonylamino-4-oxopentanoate

온도

0 °C

To a cooled to 0° C. suspension of copper (I) iodide in ether (20 mL) under N2 is slowly added methyl lithium (1.6 M solution in ether, 21.3 mmol, 13.3 mL). The mixture is stirred at 0° C. for 10 min then cooled to −78° C. A solution of 3.55 mmol of (S)-2-Benzyloxycarbonylamino-3-chlorocarbonyl-propionic acid methyl ester (Ref: Synth. Comm 1993, 23(18), 2511-2526) in 12 mL of dry THF is added drop wise. The mixture is stirred at −78° C. for 30 min then quenched by adding methanol (2 mL). The mixture is poured into saturated NH4Cl (80 mL) and extracted with ether (2×40 mL). The organic layers are dried over magnesium sulfate and concentrated in vacuum. The residue is purified over 35 g silica gel, eluted with EtOAc:Heptane (1:1) to afford (S)-2-benzyloxycarbonylamino-4-oxo-pentanoic acid methyl ester (261 mg, 26%).

1. temperaturethen cooled to −78° C
2. stirringThe mixture is stirred at −78° C. for 30 min
3. customthen quenched
4. additionby adding methanol (2 mL)
5. additionThe mixture is poured into saturated NH4Cl (80 mL)
6. extractionextracted with ether (2×40 mL)
7. dry with materialThe organic layers are dried over magnesium sulfate
8. concentrationconcentrated in vacuum
9. customThe residue is purified over 35 g silica gel
10. washeluted with EtOAc:Heptane (1:1)

ORD 기록

ord-81001c2c1a184202949ddd68da506523

출처 데이터셋

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07482448B2