HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 5-{[(Tert-butoxy)carbonyl]amino}-3-methyl-1,2-thiazole-4-carboxylic acid | HCID 60868998 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate | HCID 86706923 | 65.3% |
Reaction Steps
To a solution of 5-(tert-butoxycarbonylamino)-3-methylisothiazole-4-carboxylic acid (2.10 g, 8.13 mmol) in THF (45 mL) at 0° C. were added HATU (3.70 g, 9.76 mmol) and Hunig's base (3.15 g, 24.4 mmol). After a period of 5 min, N,O-dimethylhydroxylamine hydrochloride (1.03 g, 10.6 mmol) was added to the previous mixture. After a period of 1.5 h at rt, the resulting mixture was evaporated under reduced pressure and purified by flash chromatography (EtOAc/hexane 1:9 to 10:0) to give tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate as an oil (1.60 g). LRMS (M+H)+: 302 m/z.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09249161B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-f2f96cd76e88422e958e72a8cbfa8514 |
| Source note | uspto-grants-2016_02 |