Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acid | HCID 23508315 | — |
| Reactant | HCID 86760352 | HCID 86760352 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69417847 | HCID 69417847 | — |
Reaction Steps
In DMF (10 ml), 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (282 mg, 1.00 mmol), 6-((2S,4S)-4-fluoro-2-pyrrolidinylmethoxy)hexanoate (247 mg, 1.00 mmol), EDC•HCl (288 mg, 1.50 mmol), HOBT (203 mg, 1.50 mmol) and triethylamine (0.70 ml, 5.00 mmol) were stirred at room temperature for 22 hours. The reaction mixture was poured in ice water (50 ml), followed by extraction with ethyl acetate. The extract was washed with ice water and saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue thus obtained was purified by thin-layer silica gel chromatography, followed by separation by using chloroform/acetone (10/1), whereby the title compound (330 mg, 65%) was obtained as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07157487B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-21b6efb3bc764edcb5c8046868974a29 |
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| Source note | uspto-grants-2007_01 |
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