HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Boc-Azetidine-3-carboxylic acid | HCID 2755981 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate | HCID 21306970 | 99% |
Reaction Steps
To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (2.00 g, 9.94 mmol) in THF (50 mL) was added EDCl (2.10 g, 10.93 mmol), HOBt (1.48 g, 10.93 mmol), and N,N-diisopropylethylamine (5.19 mL, 29.82 mmol). The mixture was stirred at rt for 15 min. N,O-dimethylhydroxylamine hydrochloride (1.16 g, 11.93 mmol), was added and stirring continued for 64 h. The crude reaction was purified via ISCO® chromatography using 3:1 ethyl/hexanes to afford 2.4 g (99%) of the desired product, which was used without further characterization.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431695B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-b4b349dc9b0e4ad5add8512f45dc6877 |
| Source note | uspto-grants-2013_04 |