Acetic Acid → HCID 15385775, compound

HRID 1858350Notes

Reaction equation

HRID 1858350 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[CH2:10][CH2:11][C@@H:12]2[O:20][C:21](=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:31][CH2:32][O:33]C)[CH:4]=[CH:5]2.O.[C:36](O)(=O)C>>[C:32]([O:31][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](=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:11][CH2:10][C@@H:9]35)(=[O:33])[CH3:36]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 15385774HCID 15385774, compound

Product 1

HCID 15385775HCID 15385775, compound

Conditions

Temperature
100 °C

Procedure

4,5α-epoxy-6α-((5-methoxycarbonyl-valeryl)-oxy)-3-methoxymethoxy-17-methyl-morphinane (0.43 g, 0.91 mmol) was mixed with H2O (15 ml) and glacial acetic acid (15 ml) and stirred for 6 hours at 100° C. The mixture was then evaporated down at 40° C. using a Rotavapor and the residue obtained was purified by flash chromatography (60 g silical gel; CH2Cl2 /MeOH=9/1). The product was dissolved in H2O (6 ml) and glacial acetic acid (0.6 ml) and lyophilised. Yield: 0.221 g (0.45 mmol, 49.7%).

Workup

  1. customThe mixture was then evaporated down at 40° C.
  2. customthe residue obtained
  3. customwas purified by flash chromatography (60 g silical gel; CH2Cl2 /MeOH=9/1)
  4. dissolutionThe product was dissolved in H2O (6 ml)

Sources & evidence

ORD record
ord-f962882be8954e96a31f6cdee28e97fa
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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