Potassium Carbonate → HCID 70530903, compound

HRID 2166941Notes

Reaction equation

HRID 2166941 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15].C([O-])([O-])=O.[K+].[K+].Cl[C:30]1[N:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:33]=[N:32][N:31]=1>CN(C=O)C>[O:12]1[CH:13]2[C@@:5]34[CH2:4][CH2:3][N:2]([CH3:1])[C@@H:19]([C@:18]3([OH:21])[CH2:17][CH2:16][C:14]2=[O:15])[CH2:20][C:7]2=[C:6]4[C:11]1=[C:10]([O:22][C:30]1[N:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:33]=[N:32][N:31]=1)[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 5284604Oxymorphone

Product 1

HCID 70530903HCID 70530903, compoundYield 134%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.4 g (79.6 mmol) oxymorphone, 24 g (173.6 mmol) anhydrous K2CO3 and 14.55 g (80.1 mmol) 5-chloro-1-phenyl-1H-tetrazole in 300 ml dry DMF was stirred at room temperature under argon for 20 hours. Then the reaction mixture was filtered, washed with CHCl3 and the filtrate was evaporated in vacuo. The oily residue was dissolved in 200 ml CHCl3, extracted with 1 N NaOH, water and brine. The organic layer was dried and evaporated to give 47.5 g of an oil, which was converted to the oxalate salt to yield 41.5 g (91%) of 4,5-epoxy-14-hydroxy-N-methyl (-3-(1-phenyl-1H-5-tetrazolyloxy) morphinan-6-one.(CO2H)2.2H2O, m.p. 143°-148°. The base was crystallized with ethyl acetate, m.p. 99°-102°, [α]D --179.0° (C 0.83, CHCl3).

Workup

  1. filtrationThen the reaction mixture was filtered
  2. washwashed with CHCl3
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe oily residue was dissolved in 200 ml CHCl3
  5. extractionextracted with 1 N NaOH, water and brine
  6. customThe organic layer was dried
  7. customevaporated

Sources & evidence

ORD record
ord-6172571d02384a0bb6123b20aa6d43ed
Source dataset
uspto-grants-1983_06
Patent number
US04390699

Reaction notes

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