반응 #158066

반응 방정식

4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoic acid

tBuOH

EDCI

→

tert-butyl 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoate

수율 38.0%

용매

DCM

반응 조건

후처리

1. 1
   기타The reaction is quenched with water
2. 2
   기타the organic layer is separated
3. 3
   농축concentrated
4. 4
   기타The residue is purified by flash column chromatography on silica gel

실험 절차

A solution of 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoic acid (250 mg, 0.703 mmol), tBuOH (0.135 ml, 1.407 mmol), EDCI (270 mg, 1.407 mmol) and 4-dimethylaminopyridine (86.0 mg, 0.704 mmol) in DCM (7 ml) is allowed to stir at room temperature under nitrogen for 62 hours. The reaction is quenched with water, and the organic layer is separated and concentrated. The residue is purified by flash column chromatography on silica gel to give tert-butyl 4-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)butanoate (110 mg); HPLC retention time=1.77 minutes (condition B); MS (ES+)=412.1 (m+1) 300.0 (m-tBux2+3; 100%); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.41 (s, 9 H) 1.47 (s, 9 H) 2.36 (A of ABX, Jab=15.5 Hz, Jax=6.2 Hz, 1 H) 2.44 (B of ABX, Jab=15.5 Hz, Jbx=5.6 Hz) 2.82-2.94 (m, 2 H) 4.11-4.17 (m, 1 H) 5.08-5.10 (m, 1 H) 7.25-7.34 (m, 3H) 7.41-7.44 (m, 2 H) 7.51-7.58 (m, 4 H).

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