HCID 19887359, compound → HCID 19887363, compound

HRID 654455Notes

Reaction equation

HRID 654455 reaction equation
[C:1]1([C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][CH2:9][N:10]2[CH2:25][CH2:24][C:13]3([O:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH3:21])[C:14]3(O)[CH3:22])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.C(OC(=O)C)(=O)C>[C:1]1([C:7]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:8][CH2:9][N:10]2[CH2:25][CH2:24][C:13]3([O:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH3:21])[C:14]3=[CH2:22])[CH2:12][CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 19887359HCID 19887359, compound

Product 1

HCID 19887363HCID 19887363, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

12.6 g of 8-(3,3-diphenyl-2-propenyl)-4-hydroxy-4-methyl-2-oxo-3-propyl-1-oxa-3,8-diazaspiro[4,5]decane are refluxed in a mixture of 126 ml of acetic acid and 5.7 ml of acetic anhydride under nitrogen while stirring for 4 to 5 hours, then the solvent is distilled off under reduced pressure. The residue is made alkaline by adding 5% by weight aqueous sodium hydroxide solution and extracted with benzene. After washing the benzene phase with water to neutral and drying over anhydrous sodium sulfate, benzene is evaporated under reduced pressure and the remaining crude product is recrystallized from ethanol to give the title compound in 85.7% yield, m.p.: 126°-127° C.

Workup

  1. distillationthe solvent is distilled off under reduced pressure
  2. additionby adding 5% by weight aqueous sodium hydroxide solution
  3. extractionextracted with benzene
  4. washAfter washing the benzene phase with water to neutral and
  5. dry with materialdrying over anhydrous sodium sulfate, benzene
  6. customis evaporated under reduced pressure
  7. customthe remaining crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-6e85f3da00594698bf24122f0b076c66
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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