Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 67467711 | HCID 67467711 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 70171213 | HCID 70171213 | 27% |
Reaction Steps
To a stirring solution of 3-(2,3-dimethoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)-2,2-dimethylpropanoic acid (100 mg, 0.25 mmol) in dichloromethane (10 mL) was added 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC. HCl) (71.6 mg, 0.375 mmol), triethylamine (1 mL, 0.75 mmol) and 1-hydroxybenzotriazole hydrate (HOBT) (76.5 mg, 0.50 mmol) and stirred for 10 min. To this isopropyl amine (59 mg, 1.00 mmol) was added and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-50% ethyl acetate in pet ether) afforded the title compound as a solid (27 mg, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051290B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-5e54f03b349846d0bdd4f2273381cecf |
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| Source note | uspto-grants-2015_06 |
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