HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | cis-2-((tert-Butoxycarbonyl)amino)cyclohexanecarboxylic acid | HCID 1512487 | — |
| Reactant | Aminoacetonitrile hydrochloride | HCID 11491918 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate | HCID 60098559 | 99.9% |
Reaction Steps
To 5.05 g (20.75 mmol) of the acid of step 2 dissolved in 40 mL DMF was added 1.92 g (20.75 mmol) aminoacetonitrile hydrochloride, 3.98 g (20.75 mmol) of EDCI, 2.80 g (20.75 mmol) of HOBT and 7.98 mL (72.63 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 obtain 5.83 g of the crude tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07300934B2 |
| Source dataset | uspto-grants-2007_11 |
| ORD ID | ord-e9c9edff08e2477883cbfbb58f3a70ef |
| Source note | uspto-grants-2007_11 |