Hydrochloric Acid → HCID 18756204, compound

HRID 433933Notes

Reaction equation

HRID 433933 reaction equation
[OH:1][CH:2]([C:6]([O:19]/[CH:20]=[CH:21]/[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[H-].[Na+].[CH3:31][C:32]1[CH:37]=[C:36]([CH3:38])[N:35](S(C)(=O)=O)[CH2:34][N:33]=1.Cl>CN(C=O)C.O>[CH3:31][C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([O:1][CH:2]([C:6]([O:19]/[CH:20]=[CH:21]/[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([OH:5])=[O:4])[N:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 18756197HCID 18756197, compoundHCID 18756228HCID 18756228, compound

Product 1

HCID 18756204HCID 18756204, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.12 g (3 mmol) of 2-hydroxy-3-(3-phenyl-(2E)-propenoxy)-3,3-diphenylpropionic acid were added to a suspension of 432 mg (9 mmol, 50%) of NaH in 20 ml of DMF, and the mixture was stirred at room temperature for 10 minutes. 614 mg (3.3 mmol) of 4,6-dimethyl-1-methylsulfonylpyrimidine were added, and the mixture was stirred for 16 hours, then diluted with 200 ml of water, acidified with 1 N hydrochloric acid and extracted with ether. The ether phase was extracted with 1 N sodium hydroxide solution, the aqueous phase was again acidified, and the product was extracted with ether. The organic phase was dried over magnesium sulfate and filtered, and the solvent was distilled off. The residue was recrystallized from ether/hexane, and 927 mg (65%) of crystalline product were isolated.

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. extractionextracted with ether
  3. extractionThe ether phase was extracted with 1 N sodium hydroxide solution
  4. extractionthe product was extracted with ether
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-0fd3300d67174e79ab007433ce6fc72e
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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