Potassium Carbonate → HCID 14099453, compound

HRID 569783Notes

Reaction equation

HRID 569783 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[O:15]1[C:19]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[O:15]1[C:19]2([CH2:24][CH2:23][N:22]([C:2]3[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=3)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 14099453HCID 14099453, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 19.6 g of 4-fluoro-γ-oxobenzenebutanoic acid [prepared by following the procedure of W. Adcock and M. J. S. Dewar, J. Amer. Chem. Soc., 89, 2(1967)], 14.3 g of 1,4-dioxa-8-azaspiro[4,5]decane and 13.9 g of anhydrous K2CO3 in 75 ml of DMSO is heated at 100° C. for 18 hours and cooled. The reaction mixture is filtered and the residue is washed with DMSO. The filtrate and the washings are diluted with 300 ml of water and the pH of the solution is adjusted to 6. The solid is filtered, washed with water, and air-dried to yield 15.0 g of 4-(1,4-dioxa-8-azaspiro [4,5]-dec-8-yl)-γ-oxobenzenebutanoic acid as off-white powder, mp 130°-131° C.

Workup

  1. customprepared
  2. temperaturecooled
  3. filtrationThe reaction mixture is filtered
  4. washthe residue is washed with DMSO
  5. additionThe filtrate and the washings are diluted with 300 ml of water
  6. filtrationThe solid is filtered
  7. washwashed with water
  8. customair-dried

Sources & evidence

ORD record
ord-7e0e41d029d144eb8158215f40621b24
Source dataset
uspto-grants-1988_03
Patent number
US04734415

Reaction notes

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