Methanamine, N-methoxy-, hydrochloride (1:1) → trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide

참여 물질

역할	이름	HCID	투입량
반응물	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	trans-2-Phenylcyclopropanecarboxylic acid	HCID 237413	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
용매	Water	HCID 962	—
용매	Dimethylformamide	HCID 6228	—
생성물	trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide	HCID 15141060	42%

반응 조건

온도	25 °C

반응 단계

To a stirred solution of 35 (117.5 g, 724.48 mmol, 1.00 equiv) in DMF (1.2 L) under N2 was added methoxy(methyl)amine hydrochloride (82.3 g, 844.10 mmol, 1.17 equiv), HATU (329 g, 775.58 mmol, 1.07 equiv), and DIPEA (117.5 mL). The reaction mixture was stirred under N2 at 25° C. overnight and then diluted with water (700 mL). The organic phase was extracted with EtOAc (3×1 L), and the combined organic layers were washed with water (3×1 L) and brine (1×1 L), dried (Na2SO4), filtered and concentrated in vacuo. The residue purified by SiO2 chromatography and eluted with EtOAc/petroleum ether (10 to 50% EtOAc) to afford 62.5 g (42%) of trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide (37) as a light yellow oil.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08637537B2
출처 데이터셋	uspto-grants-2014_01
ORD ID	ord-117500c628e149d69f42b203e2b8eb9b
출처 메모	uspto-grants-2014_01