반응 #933008
ord-35fde9e90d08493f9cc615afdf27ecb2
반응 방정식
용매
반응 조건
후처리
- 1온도The mixture was refluxed for 5 h
- 2온도cooled
- 3추출extracted with 150 mL CHCl3 (3×50 mL)
- 4건조The combined CHCl3 extracts were dried (MgSO4)
- 5기타evaporated
- 6기타was chromatographed on a column of silica gel (approx. size 40 microns)
- 7기타evaporated
- 8기타the residue recrystallized from hexane-petroleum ether
- 9기타IR (KBr): No C=O absorption at 1720 cm-1
실험 절차
Naltrexone hydrochloride (1.134 g, 3 mmol) was added to a solution of CH3ONH2HCl (0.33 g, 3.9 mmol) in 15 mL MeOH containing 3.2 mL 10% aqueous NaOH. The mixture was refluxed for 5 h, cooled, diluted with approximately 100 mL H2O and extracted with 150 mL CHCl3 (3×50 mL). The combined CHCl3 extracts were dried (MgSO4) and evaporated. TLC showed that the reaction was incomplete and hence the reaction was repeated as before using the mixture, CH3ONH2HCl (0.165 g, 1.9 mmol) and 0.8 mL of 10% aqueous NaOH. After workup the product was chromatographed on a column of silica gel (approx. size 40 microns) using EtOAC-EtOH-NH4OH (100:1:0.5) as eluent. The fractions were combined, evaporated and the residue recrystallized from hexane-petroleum ether. Yield: 0.55 g (49.6%). mp 172°-173° C. IR (KBr): No C=O absorption at 1720 cm-1 ; 1H NMR: (CDCl3)δ4.95 (s, C5H), 3.82 (s, OCH3); Rf: silica gel 60 in EtOAc-EtOH-NH4OH (100:1:1) 0.40. Anal. Caled for C21H26N2O4 : C, 68.09; H, 7.07; N, 7.56. Found: C, 67.96; H, 7.11; N, 7.55.