HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid | HCID 688396 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate | HCID 15234151 | — |
Reaction Steps
To a solution of 1-(tert-butoxycarbonylamino)cyclopropanecarboxylic acid (11.00 g, 54.7 mmol, 1.0 eq) in methylene chloride at 0° C. was added N,O-dimethyl hydroxylamine HCl (5.9 g, 60.4 mmol, 1.1 eq), TEA (13.82 g, 13.6 mmol, 2.5 eq) and HATU (22.90 g, 60.2 mmol, 1.1 eq). The resulting reaction mixture was stirred at room temperature under an N2 atmosphere overnight. After TLC showed reaction was completed, the reaction mixture was concentrated, diluted with water and extracted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4 and concentrated to get the desired product as a white solid. Yield: 13.00 g (97.52%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309558B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-f02f3b3743e9438689d2b974566c119b |
| Source note | uspto-grants-2012_11 |