Diisopropylethylamine → (S)[[2-Benzyloxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acid methyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylethylamine	HCID 81531	—
反応物	HOAt	HCID 181649	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
反応物	Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinate	HCID 10889780	—
反応物	Z-His(Trt)-OH	HCID 15545280	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Dichloromethane	HCID 6344	—
生成物	(S)[[2-Benzyloxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acid methyl ester	HCID 69904020	97%

反応手順

The product from Step 1 (0.67 g, 2.5 mmol) was dissolved in methylene chloride (10 mL) and Cbz-His(Trt)-OH (1.46 g, 2.75 mmol) was then added, followed by diisopropylethylamine (1.3 mL, 7.5 mmol), HATU (1.05 g, 2.76 mmol), HOAt (0.374 g, 2.75 mmol), and dimethylformamide (10 mL). The reaction was stirred overnight at room temperature. The solution was concentrated, the residue taken up in ethyl acetate and washed three times with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo to give a white solid; 1.8 g (97% yield). MS-APCI: M+1=747.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US06369034B1
出典データセット	uspto-grants-2002_04
ORD ID	ord-9fc0a3a4702141aead5356724a700604
出典メモ	uspto-grants-2002_04