반응 #87130

반응 방정식

triphenylphosphine

imidazole

Cbz-L-Ser-OMe

iodide

→

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

수율 57.0%

용매

DCM

DCM

반응 조건

후처리

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

실험 절차

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.

출처