Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dicyclohexylamine | HCID 7582 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 2-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acid | HCID 51039954 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 44251013 | HCID 44251013 | — |
Reaction Steps
1.0 g (3.3 mmol) of (2-([4-chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethoxy)acetic acid, a catalytic quantity of DMF, and 505 mg (3.98 mmol) of oxalyl chloride were stirred at 0° C. for 1.5 hours in 10 mL of THF. After completion of the reaction, the solvent was distilled off under reduced pressure. 0.66 g (3.6 mmol) of dicyclohexylamine, and 10 mL of DMA were added to this residue, and stirred at room temperature for 2 hours. After completion of the reaction, water was added, and the precipitated crystals were collected by filtration and dried to give the crude product of 5-chloro-2-(([2-(dicyclohexylamino)-2-oxoethoxy]acetyl)amino)benzoic acid.methyl ester. The crude product was then used in the subsequent stage without being purified.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415479B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-9e1f7542351a44489c8189fd1c30ad6d |
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| Source note | uspto-grants-2013_04 |
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