Sodium Hydroxide → HCID 54348545, compound

HRID 1740883Notes

Reaction equation

HRID 1740883 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@H:10]([N:24]([CH3:38])[C:25](=[O:37])[CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:39])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@H:10]([N:24]([CH3:38])[C:25](=[O:37])[CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:39])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86754662HCID 86754662, compound

Product 1

HCID 54348545HCID 54348545, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

360 mg of the 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-methyl-3-nitrocinnamamido)morphinan 78 and 1.07 g of stannous chloride dihydrate were dissolved in 7.5 ml of ethanol followed by heating to 70° C. and stirring for 2 hours. After cooling the reaction mixture to room temperature, 2 N aqueous sodium hydroxide was added while cooling with ice to neutralize followed by extraction with dichloromethane. The organic layers were combined and washed with saturated brine followed by drying and concentration. Inorganic substances were removed by chromatographic filtration [silica gel; chloroform:methanol (9:1)]. The resulting unpurified target compound was converted to a 2 hydrochloride to obtain 310 mg. ##STR66##

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. temperaturewhile cooling with ice
  3. extractionto neutralize followed by extraction with dichloromethane
  4. washwashed with saturated brine
  5. customby drying
  6. concentrationconcentration
  7. customInorganic substances were removed by chromatographic filtration [silica gel; chloroform:methanol (9:1)]
  8. customto obtain 310 mg

Sources & evidence

ORD record
ord-962ea25e69da40f998d582579d5b5562
Source dataset
uspto-grants-1999_10
Patent number
US05972953

Reaction notes

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