Tert-Butylamine → (S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	Tert-Butylamine	HCID 6385	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine	HCID 98763	—
反応物	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
溶媒	Diethyl Ether	HCID 3283	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	(S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester	HCID 11809380	153.7%

反応条件

温度	0 °C

反応手順

A solution of N-(tert-Butyloxycarbonyl)-O-benzyl-L-tyrosine (Bachem, 2.00 g, 5.38 mmol) in 20 mL of DMF was cooled to 0C and treated with iPr2NEt (1.5 mL) followed by HBTU (2.04 g, 5.38 mmol). The resulting suspension was stirred for 30 minutes at 0° C. and then treated with tert-butylamine (0.48 g, 6.56 mmol). The reaction mixture was stirred for 1 hour at 0° C. and warmed to room temperature. The reaction mixture was poured into Et2O and washed sequentially with saturated aqueous NaHCO3 solution, and saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate) to give the product (2.65 g).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US06423689B1
出典データセット	uspto-grants-2002_07
ORD ID	ord-62054830a605401f9c70966e633748bd
出典メモ	uspto-grants-2002_07