反応 #87130

反応方程式

triphenylphosphine

imidazole

Cbz-L-Ser-OMe

iodide

→

(R)-methyl 2-(benzyloxycarbonylamino)-3-iodopropanoate

収率 57.0%

溶媒

DCM

DCM

反応条件

後処理

1. 1
   その他The cooling bath was removed
2. 2
   温度After the mixture was re-cooled to 0° C.
3. 3
   workup.ADDITIONAfter the addition
4. 4
   その他the cooling bath was removed
5. 5
   温度to warm to ambient temperature
6. 6
   workup.STIRRINGstirred for 1.5 h
7. 7
   ろ過The mixture was filtered
8. 8
   濃縮the filtrate was concentrated
9. 9
   その他to remove most of the solvent
10. 10
    workup.ADDITIONMTBE (400 mL) was added to the residue
11. 11
    ろ過the mixture was filtered
12. 12
    その他to remove triphenylphosphine oxide
13. 13
    濃縮The filtrate was concentrated
14. 14
    その他the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=50:1 to 10:1)

実験手順

A mixture of triphenylphosphine (23.3 g, 0.890 mol) and imidazole (6.0 g, 0.89 mol) in DCM (100 mL) was cooled to 0° C. and iodide (22.6 g, 0.890 mol) was added in small portions over 0.5 h. The cooling bath was removed and the mixture was stirred for 0.5 h. After the mixture was re-cooled to 0° C., a solution of Cbz-L-Ser-OMe 15.0 g, 0.590 mol) in DCM (100 mL) was added dropwise. After the addition, the cooling bath was removed and the mixture was allowed to warm to ambient temperature and stirred for 1.5 h. The mixture was filtered and the filtrate was concentrated to remove most of the solvent. MTBE (400 mL) was added to the residue and the mixture was filtered to remove triphenylphosphine oxide. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=50:1 to 10:1) to afford (R)-methyl 2-(benzyloxycarbonylamino)-3-iodopropanoate (12.3 g, 57% yield) as a colorless solid.

出典