Sodium Hydroxide → HCID 19887357, compound

HRID 654451Notes

Reaction equation

HRID 654451 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:30][CH2:29][C:15]3([O:19][C:18](=[O:20])[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[C:16]3(O)[CH3:27])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:30][CH2:29][C:15]3([O:19][C:18](=[O:20])[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[C:16]3=[CH2:27])[CH2:14][CH2:13]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 19887346HCID 19887346, compound

Product 1

HCID 19887357HCID 19887357, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

20.4 g of 8-[4,4-bis(4-fluorophenyl)-3-butenyl]-3-cyclohexyl-4-hydroxy-4-methyl-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane are boiled with 1.52 g of p-toluenesulfonic acid monohydrate in 204 ml of xylene while stirring in an apparatus fitted with a water-trap and azeotropically distilling off the water formed in the reaction. After the termination of the reaction (about 2 hours) the reaction mixture is cooled down and its pH value is adjusted to 9-10 by adding 5% by weight aqueous sodium hydroxide solution. Then, the organic phase is washed with water to neutral, dried over anhydrous sodium sulfate and evaporated under reduced pressure. After recrystallizing the residue from a mixture of benzene and ethanol, the title product is obtained in 90.3% yield, m.p.: 145°-146° C.

Workup

  1. customfitted with a water-trap
  2. distillationazeotropically distilling off the water
  3. customformed in the reaction
  4. customAfter the termination of the reaction (about 2 hours) the reaction mixture
  5. temperatureis cooled down
  6. washThen, the organic phase is washed with water to neutral,
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customAfter recrystallizing the residue
  10. additionfrom a mixture of benzene and ethanol

Sources & evidence

ORD record
ord-91ff0e2d157e4306987beca73d39daed
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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