HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl N-((6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetyl)glycinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Glycine ethyl ester, hydrochloride | HCID 2723640 | — |
| Reactant | (6-((2,4-Dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetic acid | HCID 89767783 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | Ethyl N-((6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetyl)glycinate | HCID 89767793 | 85.5% |
Reaction Steps
To a mixture of (6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetic acid (150 mg) in DMF (dry) (3.0 mL) were added ethyl 2-aminoacetate hydrochloride (57.0 mg), HOBt (71.7 mg), EDCI (102 mg) and triethylamine (0.171 mL). The mixture was stirred at room temperature for 17 h. The mixture was diluted with saturated aqueous NaHCO3 and water. The mixture was extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was washed with hexane to give the title compound (158 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238639B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-adb28dc506054ce58ed7089073cf0241 |
| Source note | uspto-grants-2016_01 |