Acetic Acid → HCID 20638250, compound

HRID 1858355Notes

Reaction equation

HRID 1858355 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:27][CH2:28][O:29]C)[CH:4]=[CH:5]2.O.[C:32](O)(=O)C>>[C:28]([O:27][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:18]([CH3:19])[CH2:17][CH2:16][C@:14]45[C:15]=2[C:2]=1[O:1][C@H:13]4[C@@H:12]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH:11]=[CH:10][C@@H:9]35)(=[O:29])[CH3:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 15351904HCID 15351904, compound

Product 1

HCID 20638250HCID 20638250, compound

Conditions

Temperature
100 °C

Procedure

4,5α-Epoxy-3-methoxymethoxy-17-methyl-6α-((2-pyridyl)-oxy)-morphinan-7-ene (0.54 g, 1.33 mmol) is mixed with H2O (20 ml) and glacial acetic acid (20 ml) and stirred for 2.5 hours at 100° C. The mixture is then concentrated by rotary evaporation in a Rotavapor at 40° C. and the residu e obtained is purified by flash chromatography (90 g silica gel; CH2Cl2 /MeOH=9/1). The product is dissolved in H2O (7 ml) and glacial acetic acid (0.7 ml) and lyophilised. Yield: 0.436 g (1.03 mmol, 77.6%)

Workup

  1. concentrationThe mixture is then concentrated by rotary evaporation in a Rotavapor at 40° C.
  2. customthe residu e obtained
  3. customis purified by flash chromatography (90 g silica gel; CH2Cl2 /MeOH=9/1)
  4. dissolutionThe product is dissolved in H2O (7 ml)

Sources & evidence

ORD record
ord-517de0975233448b8d605ec4463aa6bc
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

Loading…