Sodium hydride → (1-{2-[5-(4-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl)-2-methyl-propyl)-carbamic acid methyl ester

https://huagongshe.com/ko/reaction/417488

참여 물질

역할	이름	HCID	투입량
반응물	Sodium hydride	HCID 24758	—
반응물	2-Chloromethyl 2-(trimethylsilyl)ethyl ether	HCID 2724271	—
반응물	Methyl (1-(2-(4-(4-bromophenyl)-1H-imidazol-2-YL)pyrrolidin-1-YL)-3-methyl-1-oxobutan-2-YL)carbamate	HCID 66620141	—
용매	Dimethylformamide	HCID 6228	—
용매	Ethyl Acetate	HCID 8857	—
용매	Ammonium Chloride	HCID 25517	—
생성물	(1-{2-[5-(4-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl)-2-methyl-propyl)-carbamic acid methyl ester	HCID 66620156	71.4%

반응 단계

(1-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (2.6 g, 5.8 mmol) in DMF (60 mL) was treated with NaH (60% dispersion in mineral oil, 256 mg, 6.4 mmol) in one portion. After 5 min, the mixture was treated with SEMCl (1.08 mL, 6.1 mmol) in 0.1 mL portions over 10 min. The reaction was stirred for 2 hours and diluted with saturated NH4Cl solution (50 mL) and EtOAc (100 mL). The organic layer was washed with H2O (3 50 mL) and brine (50 mL). The solution was dried over MgSO4 and subjected to a 120 g SiO2 COMBIFLASH column (0-100% EtOAc-hexanes gradient) to afford (1-{2-[5-(4-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (2.4 g, 71%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08088368B2
출처 데이터셋	uspto-grants-2012_01
ORD ID	ord-8823dceadbe94b36a7256b21297663cd
출처 메모	uspto-grants-2012_01