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

関与物質

役割	名称	HCID	仕込み量
反応物	1-Hydroxybenzotriazole	HCID 75771	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
反応物	N-(tert-Butoxycarbonyl)-L-cyclohexylglycine	HCID 7004938	—
反応物	(S)-2-(3-phenoxy-phenyl)-pyrrolidine	HCID 59787976	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Sodium chloride; water	HCID 57417360	—
生成物	{(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester	HCID 59787985	68.7%

反応手順

(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).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08207183B2
出典データセット	uspto-grants-2012_06
ORD ID	ord-72d8606d0cc04e7c99c8526d137f18a3
出典メモ	uspto-grants-2012_06