Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethynylcyclohexylamine | HCID 121691 | — |
| Reactant | 4-[4-(2-Methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid | HCID 9863428 | — |
| Reactant | N,N-bis(2-oxo-3oxazolidinyl)phosphoramidic chloride | HCID 19975454 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15296375 | HCID 15296375 | 31.3% |
Reaction Steps
A mixture of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid (1.772 g, 5 mmole), triethylamine (1.518 g, 15 mmole), and N,N-bis(2-oxo-3-oxazolidinyl)phosphoramidic chloride (1.527 g, 6 mmole) was stirred in methylene chloride (80 mL) under exclusion of moisture at ambient temperature for 30 minutes, after which 1-ethynylcyclohexylamine (0.668 g, 6 mmole) was added at once at 0° C. The reaction mixture was stirred at room temperature overnight, washed with water (2×100 mL), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Chromatography on silica gel with methanol/chloroform as eluant, followed by trituration from diethyl ether/hexane gave 0.72 g of the title compound as the 0.12 methylene chloride solvate, m.p. 127°-9° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05451584 |
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| Source dataset | uspto-grants-1995_09 |
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| ORD ID | ord-60c6e1ec93c1479b93785bebe70e946e |
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| Source note | uspto-grants-1995_09 |
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