HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Nitrobenzoyl chloride → (R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Nitrobenzoyl chloride | HCID 11875 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | methyl (2R)-2-amino-2-cyclohexylacetate hydrochloride | HCID 56777252 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester | HCID 68726619 | 98.1% |
Reaction Steps
To a mixture of 2-nitrobenzoyl chloride (0.5 mL, 3.69 mmol) and (R)-amino-cyclohexyl-acetic acid methyl ester hydrochloride (1.0 g, 4.82 mmol), (prepared according to example A), in dichloromethane (10 mL) is added diisopropyl ethylamine (DIPEA) (1.5 mL, 8.61 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 40% EtOAc in Hexane as the eluent to afford (R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester (1.16 g, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08377949B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-f98f80d3a0c34d2784e468ed5d3a17ab |
| Source note | uspto-grants-2013_02 |