Sodium Hydroxide → (S)-benzyl 4-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)piperidine-1-carboxylate

関与物質

役割	名称	HCID	仕込み量
反応物	Sodium Hydroxide	HCID 14798	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	Boc-L-methionine	HCID 89857	—
反応物	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
反応物	4-Amino-1-N-Cbz-piperidine	HCID 17846640	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	(S)-benzyl 4-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)piperidine-1-carboxylate	HCID 86688073	100%

反応手順

A solution of HBTU (8.1 g, 21 mmol), (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoic acid (5.3 g, 21 mmol) and DIEA (8.2 mL, 47 mmol) in DMF (50 mL) was stirred at ambient temperature for 30 minutes. Benzyl 4-aminopiperidine-1-carboxylate (5.0 g, 21 mmol) was added and the mixture was stirred at ambient temperature for 18 hours. The mixture was poured into 1N NaOH (500 mL) and the combined organic layers were extracted into EtOAc (500 mL). The combined organic layers were washed with 1N HCl (500 mL) and brine (500 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to yield (S)-benzyl 4-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)piperidine-1-carboxylate (10 g, 21 mmol, 100%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08754226B2
出典データセット	uspto-grants-2014_06
ORD ID	ord-03464b571e664c12a611bb3abc3d4c73
出典メモ	uspto-grants-2014_06