HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 1-(3-{2-[3-(2-Hydroxy-ethyl)-phenyl]-ethoxy}-4-methoxy-benzoylamino)-cycloheptanecarboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Methyl 1-aminocycloheptane-1-carboxylate hydrochloride | HCID 42614177 | — |
| Reactant | 3-{2-[3-(2-Hydroxy-ethyl)-phenyl]-ethoxy}-4-methoxy-benzoic acid | HCID 67170710 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Product | 1-(3-{2-[3-(2-Hydroxy-ethyl)-phenyl]-ethoxy}-4-methoxy-benzoylamino)-cycloheptanecarboxylic acid methyl ester | HCID 67170334 | 28.9% |
Reaction Steps
The compound of step 1 (280 mg, 0.885 mmol) was dissolved in DMF (1.3 ml) and HOBT (24 mg), 1-amino-cycloheptanecarboxylic acid methyl ester hydrochloride (221 mg, 1.06 mmol) and EDIA (578 mg, 4.43 mmol) were added. The mixture was cooled in an ice bath and EDC (254 mg, 1.33 mmol) was added. The mixture was stirred at room temperature for 3 days and partitioned between EA and water. The aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient) to yield the title compound (120 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618304B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-118e557d1b2141faa30a53b36814380a |
| Source note | uspto-grants-2013_12 |