반응 #86642

반응 방정식

N-BOC-tyrosine methyl ester

potassium carbonate

4-bromo-1-butene

→

(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

용매

EtOAc

DMF

EtOAc

반응 조건

후처리

1. 1
   기타partitioned with 1M hydrochloric acid
2. 2
   세척The organic phase was washed with hydrochloric acid
3. 3
   건조with brine before being dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
7. 7
   기타to yield a white solid, 3.20 g, 27%

실험 절차

N-BOC-tyrosine methyl ester (10.0 g, 33.9 mmol) was dissolved in DMF (40 mL) and potassium carbonate (5.62 g, 40.7 mmol) and 4-bromo-1-butene (4.13 mL, 40.7 mmol) were added. The mixture was stirred at rt for 18 h before being diluted with EtOAc (120 mL) and partitioned with 1M hydrochloric acid. The organic phase was washed with hydrochloric acid and then with brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 3.20 g, 27%. Rf=0.82 (1/2 EtOAc/(50/70) petroleum ether).

출처