Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 23157653 | HCID 23157653 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23157523 | HCID 23157523 | 66.3% |
Reaction Steps
To a solution of [4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)phenoxy]acetic acid (0.22 g, 0.49 mmol), N,O-dimethylhydroxylamine hydrochloride (72 mg, 0.74 mmol), triethylamine (0.12 mL, 0.86 mmol) and 1-hydroxybenzotriazole (98 mg, 0.64 mmol) in N,N-dimethylformamide (15 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (122 mg, 0.64 mmol) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-2:1) to give the title compound (160 mg, yield 66%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07786165B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-f5c5ef4185e5444d84adacd10c3421e2 |
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| Source note | uspto-grants-2010_08 |
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