Sodium Carbonate → HCID 59075090, compound

HRID 2184333Notes

Reaction equation

HRID 2184333 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=1)[OH:19].[C:28]1([CH3:37])[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[CH:18]([OH:19])[C:20]1[CH:21]=[C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH3:37])[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 59075095HCID 59075095, compound

Product 1

HCID 59075090HCID 59075090, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 7-{(R)-2-[(E)-3-(3-bromo-phenyl)-3-hydroxy-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid methyl ester, (0.2 g, 0.46 mmol) in 10 mL of DME stirred at room temperature was added Pd(Ph3P)4 (0.03 g, 0.05 eq). After stirring for 5 minutes, o-tolylboronic acid (0.12 g, 2 eq) an 2M Na2CO3 (0.6 mL, 2.5eq) were added and the mixture was refluxed overnight under N2 atmosphere. The reaction mixture was cooled to room temperature, diluted with 25% NH4Oac (10 mL), stirred for 5 minutes and then was extracted with ethyl acetate, the organic layer was dried over MgSO4 (anhydrous), concentrated under the reduced pressure and purified to yield 87 mg of 7-{(R)-2-[(E)-3-hydroxy-3-(2′-methyl-biphenyl-3-yl)-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid methyl ester.

Workup

  1. temperaturethe mixture was refluxed overnight under N2 atmosphere
  2. additiondiluted with 25% NH4Oac (10 mL)
  3. stirringstirred for 5 minutes
  4. extractionwas extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over MgSO4 (anhydrous)
  6. concentrationconcentrated under the reduced pressure
  7. custompurified

Sources & evidence

ORD record
ord-40036a4c5ad1426b913091a4da86b2b9
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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