HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl beta-alanate | HCID 192794 | — |
| Reactant | 2-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acid | HCID 2776438 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 3-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid | HCID 117920188 | 103.5% |
Reaction Steps
2-phenyl-5-trifluoromethyloxazole-4-carboxylic acid (200 mg, 0.78 mmol), EDCI (372.7 mg, 1.94 mmol), methyl 3-aminopropionate (16.7 mg, 1.17 mmol), HOBt (157.6 mg, 1.17 mmol) and ethyldiisopropylamine (352.6 mg, 2.7 mmol) dissolved in dichloromethane (15 mL) were stirred for 24 hours. The reaction mixture was diluted with aqueous NaHCO3 and extracted with dichloromethane. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography to obtain the desired compound (265 mg, 99%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321728B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-1e74dbaceb8f4781849c511d30a26ad9 |
| Source note | uspto-grants-2016_04 |