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

참여 물질

역할	이름	HCID	투입량
반응물	Tert-Butylamine	HCID 6385	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine	HCID 98763	—
반응물	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
용매	Diethyl Ether	HCID 3283	—
용매	Dimethylformamide	HCID 6228	—
생성물	(S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester	HCID 11809380	153.7%

반응 조건

온도	0 °C

반응 단계

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).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US06423689B1
출처 데이터셋	uspto-grants-2002_07
ORD ID	ord-62054830a605401f9c70966e633748bd
출처 메모	uspto-grants-2002_07