Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 2,2,5-trimethyl-1,3-dioxane-5-carboxylic Acid | HCID 11355776 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 15173281 | HCID 15173281 | 86.6% |
Reaction Steps
To a mixture of 2,2,5-trimethyl-1,3-dioxane5-carboxylic acid (1.0 g, 5.74 mmol) and DMF (10 mL) were added N,O-dimethylhydroxylamine hydrochloride (0.84 g, 8.6 mmol), 1-hydroxybenzotriazole hydrate (1.32 g, 8.6 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloric acid (1.651 g, 8.61 mmol) and triethylamine (2.39 mL, 17.2 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at room temperature for 3 hours. After the reaction was completed, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulphate, and concentrated in vacuo to give N-methoxy-N,2,2,5-tetramethyl-1,3-dioxane5-carboxylic acid amid (1.08 g, yield: 86%) as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575197B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-5f3f26661c0e47f4a312664250ab8f91 |
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| Source note | uspto-grants-2013_11 |
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