1-Hydroxybenzotriazole → {(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester

참여 물질

역할	이름	HCID	투입량
반응물	1-Hydroxybenzotriazole	HCID 75771	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
반응물	N-(tert-Butoxycarbonyl)-L-cyclohexylglycine	HCID 7004938	—
반응물	(S)-2-(3-phenoxy-phenyl)-pyrrolidine	HCID 59787976	—
용매	Dimethylformamide	HCID 6228	—
용매	Sodium chloride; water	HCID 57417360	—
생성물	{(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester	HCID 59787985	68.7%

반응 단계

(S)-2-(3-phenoxy-phenyl)-pyrrolidine (1.2 g, 5.02 mmol) is added to a solution of Boc-L-α-cyclohexylglycine (1.42 g, 5.2 mmol), HOBt (1.0 g, 7.53 mmol) and HBTU (2.86 g, 7.53 mmol) in 10 mL of DMF. Hunig's base (3.6 Ml, 20 mmol) is added and the mixture is stirred for 30 minutes. The mixture is diluted with brine (20 mL) and extracted with EtOAc (3×10 mL). The organics were combined, dried over Na2SO4, filtered, concentrated under reduced pressures and purified by silica gel column chromatography (20% EtOAc/Hexanes) to give {(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester as a white powder (1.65 g, 66%). LCMS m/z 479.2 (M+1).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08207183B2
출처 데이터셋	uspto-grants-2012_06
ORD ID	ord-72d8606d0cc04e7c99c8526d137f18a3
출처 메모	uspto-grants-2012_06