HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Nitrobenzoyl chloride → {1-[(2-Nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Nitrobenzoyl chloride | HCID 11875 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 2-[1-(aminomethyl)cyclohexyl]acetate hydrochloride | HCID 45260937 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | {1-[(2-Nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester | HCID 68725102 | 99.2% |
Reaction Steps
To a mixture of 2-nitrobenzoyl chloride (0.3 mL, 2.05 mmol) and (1-aminomethyl-cyclohexyl)-acetic acid methyl ester hydrochloride (500 mg, 2.25 mmol) (prepares according to example A) in dichloromethane (10 mL) is added DIPEA (0.75 mL, 4.02 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated and the resulting residue is purified by flash chromatography with 50% EtOAc in Hexane as the eluent to afford the desired {1-[(2-nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester (680 mg, 99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08377949B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-a7246f792cc84d279f76f489d3951dbe |
| Source note | uspto-grants-2013_02 |