Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (1,1'-Biphenyl)-4-carboxylic acid | HCID 66724 | — |
| Reactant | Methyl 4-bromo-3-oxopentanoate | HCID 9815681 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 58979133 | HCID 58979133 | 98% |
Reaction Steps
A mixture of biphenyl-4-carboxylic acid (800 g, 4.03 mol) in acetone (4.6 L) was treated with triethylamine (0.6 L, 4.3 mol, 1.07 eq) dropwise over 13 min while maintaining the temperature at 15-30° C. 4-Bromo-3-oxo-pentanoic acid methyl ester (880 g, 4.21 mol, 1.04 eq) was added dropwise over 21 min at 15-30° C. The mixture was stirred overnight at room temperature. Water (9.6 L) was added dropwise over 85 minutes at 15-30° C. The mixture was stirred for 2 h. The precipitated product was collected by filtration and washed twice with water (1 L). The product was dried under vacuum at 50° C. to afford 1291 g (98% yield, 96% HPLC purity) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07282501B2 |
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| Source dataset | uspto-grants-2007_10 |
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| ORD ID | ord-117cd3ade43c4311ba0ca646f124a3f1 |
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| Source note | uspto-grants-2007_10 |
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