HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → N-Methoxy-N-methyl-3-(2,2-dimethylpropyl)cyclobutanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-(2,2-Dimethylpropyl)cyclobutane-1-carboxylic acid | HCID 86675039 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | N-Methoxy-N-methyl-3-(2,2-dimethylpropyl)cyclobutanecarboxamide | HCID 86675040 | 101% |
Reaction Steps
3-(2,2-Dimethylpropyl)cyclobutanecarboxylic acid (75.2 g) and DMF (600 mL) were mixed. After an addition of N,O-dimethylhydroxylamine hydrochloride (51.7 g), triethylamine (92.4 mL), HOBt.H2O (81.2 g) and WSC.HCl (101.6 g) to the mixture, the mixture was stirred at RT overnight. Water was poured into the reaction and the mixture was extracted with ethyl acetate/hexane=1/1. The organic layer was washed with 1 N hydrochloric acid, water, aqueous 10 w/v % sodium carbonate and water, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (95.2 g) as a crude product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08604069B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-891fb7d8c87f4ad0b33122c0bd25cec6 |
| Source note | uspto-grants-2013_12 |