Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methylphenyl boronic acid | HCID 2733267 | — |
| Reactant | HCID 59075095 | HCID 59075095 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 59075090 | HCID 59075090 | 42.1% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06900336B2 |
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| Source dataset | uspto-grants-2005_05 |
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| ORD ID | ord-40036a4c5ad1426b913091a4da86b2b9 |
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| Source note | uspto-grants-2005_05 |
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