Sodium Chloride → HCID 19004568, compound

HRID 2225485Notes

Reaction equation

HRID 2225485 reaction equation
C([O-])=O.[NH4+].[OH:5][C:6]1[CH:29]=[CH:28][C:9](/[CH:10]=[CH:11]/[C:12]([NH:14][CH:15]2[CH2:20][CH2:19][C:18]([CH3:27])([C:21]([O:23]CC=C)=[O:22])[CH2:17][CH2:16]2)=[O:13])=[CH:8][C:7]=1[O:30][CH3:31].[Cl-].[Na+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:5][C:6]1[CH:29]=[CH:28][C:9](/[CH:10]=[CH:11]/[C:12]([NH:14][CH:15]2[CH2:20][CH2:19][C:18]([CH3:27])([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]2)=[O:13])=[CH:8][C:7]=1[O:30][CH3:31]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 2723923Ammonium formateHCID 19004772HCID 19004772, compound

Product 1

HCID 19004568HCID 19004568, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.5 of bis(triphenylphosphine)palladium dichloride and 7.5 g of ammonium formate were added to a solution of 2.81 g of allyl trans-4-(4-hydroxy-3-methoxycinnamamido)-1-methyl-1-cyclohexanecarboxylate (Example 24) in 100 ml of THF. The solution was reacted for 18 hours under an argon stream, while it was refluxed. After reaction, 150 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution, was then dried over magnesium sulfate. Then, the solvent was removed in vacuo. The oil substance thus obtained was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=1:2, the solvent was removed in vacuo, yielding 1.7 g of trans-4-(4-hydroxy-3-methoxycinnamamido)-1-methyl-1-cyclohexanecarboxylic acid (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 18 hours under an argon stream
  2. temperaturewhile it was refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed three times with an aqueous sodium chloride solution
  7. dry with materialwas then dried over magnesium sulfate
  8. customThen, the solvent was removed in vacuo
  9. customThe oil substance thus obtained
  10. washFrom the fraction eluted with hexane and ethyl acetate=1:2
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-285da9ac6d20449283f6162efb9709cd
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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