1-Hydroxybenzotriazole → trans-4-(3-Biphenyloxy) N-tert-butoxycarbonyl-L-proline 2-(N-tert-butoxycarbonylamino)ethylamide

Triethylamine (56 μL), 1-hydroxybenzotriazole (25 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg) were added to a solution of trans-4-(3-biphenyloxy)-N-tert-butoxycarbonyl-L-proline (B), (141 mg) and tert-butyl N-(2-aminoethyl)carbamate (65 mg) in dichloromethane (3 mL). After stirring at room temperature overnight, the reaction mixture was diluted with chloroform and washed with saturated sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography chloroform:methanol=100:1, v/v to give the titled compound (175 mg) as a colorless foam: 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 2.37 (m, 1H), 2.59 (m, 1H), 3.28 (m, 1H), 3.29 (s, 2H), 3.40 (m, 1H), 3.73 (m, 2H), 4.41 (m, 1H), 5.01 (m, 1H), 5.18 (m, 1H), 6.86 (m, 2H), 7.08 (s, 1H), 7.20 (d, J=7.3 Hz, 1H), 7.35 (t, J=7.3 E4z, 2H), 7.43 (t, J=7.3 Hz, 2H), and 7.56 (d, J=7.3 Hz,2H).

1. washwashed with saturated sodium hydrogen carbonate and brine
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. customevaporated in vacuo
4. customThe residue was purified by silica gel column chromatography chloroform

ORD-Eintrag

ord-c1cc5ff03e9f4460b2f598301780fada

Quelldatensatz

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06399629B1