HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → ethyl (1R,2S)-2-[(1H-indol-2-ylcarbonyl)amino]cyclohexane-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Indole-2-carboxylic acid | HCID 72899 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Ethyl (1R,2S)-2-aminocyclohexane-1-carboxylate hydrobromide | HCID 122236269 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ethyl (1R,2S)-2-[(1H-indol-2-ylcarbonyl)amino]cyclohexane-carboxylate | HCID 71206173 | — |
Reaction Steps
To 300 mg (1.19 mmol) of ethyl (1R,2S)-2-aminocyclohexanecarboxylate HBr salt (Xu, Daquiang et al., Tetrahedron:Asymmetry (1988), 9(10) 1635) dissolved in 8 mL DMF was added 192 mg (1.19 mmol) of indole-2-carboxylic acid, 228 mg (1.19 mmol) of EDCI, 161 mg (1.19 mmol) of HOBT and 0.458 mL (4.16 mmol) of N-methylmorpholine. The reaction mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated to provide ethyl (1R,2S)-2-[(1H-indol-2-ylcarbonyl)amino]cyclohexane-carboxylate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06747053B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-c296b9452cbc451c8f34b4811fdff14f |
| Source note | uspto-grants-2004_06 |