Diisopropylethylamine → (9H-Fluoren-9-yl)methyl(S)-1-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-ylcarbamate

참여 물질

역할	이름	HCID	투입량
반응물	Diisopropylethylamine	HCID 81531	—
반응물	N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanine	HCID 6364642	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	(S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine	HCID 67075196	—
용매	Water	HCID 962	—
용매	Dimethylformamide	HCID 6228	—
용매	Ethyl Acetate	HCID 8857	—
생성물	(9H-Fluoren-9-yl)methyl(S)-1-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-ylcarbamate	HCID 86652577	71.2%

반응 단계

According to the procedure described in the synthesis method of Compound III-1, (S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine (Compound IX-2) 12.9 g (45 mmol) and Fmoc-Ala-OH 18.3 g (58.8 mmol) were dissolved in DMF (200 ml). HATU (O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (25.6 g, 67.5 mmol) and DIEA (diidopropylethylamine) (8.7 g, 67.5 mmol) were added at room temperature. The mixture was stirred overnight at room temperature. The mixture was poured into water (800 ml). The solution was extracted with EA (ethyl acetate) (300 ml×3). The combined extracts were dried over Na2SO4 and then filtered. The solvent was removed in vacuo. The residue was purified by column chromatography on silica gel with PE (petroleum ether): EA=30:1 to 5:1 to give the title compound 18.6 g, (yield 71%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08455488B2
출처 데이터셋	uspto-grants-2013_06
ORD ID	ord-985edd7f69d542948c0927070ea2cd51
출처 메모	uspto-grants-2013_06