Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Carbamate | HCID 11722 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | HCID 9866203 | HCID 9866203 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | HCID 22013854 | HCID 22013854 | 61.4% |
Reaction Steps
2-Methoxycarbonyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid (2.00 g, 4.89 mmol) obtained in Example 1 was dissolved in benzene (15 ml), and thionyl chloride (392 μl, 5.38 mmol) was added at room temperature. The mixture was refluxed under heating for 1.5 hr and the solvent was evaporated. The residue was dissolved in toluene (6 ml), and methyl carbamate (440 mg, 5.87 mmol) was added. at room temperature. The mixture was stirred at 80-90° C. for 30 min. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (developing solvent; chloroform: methanol=30:1). The obtained white solid was recrystallized from methanol to give the title compound (1.40 g, yield 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06204277B1 |
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| Source dataset | uspto-grants-2001_03 |
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| ORD ID | ord-b5bbd020914c41c8a74a53a3526a9112 |
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| Source note | uspto-grants-2001_03 |
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