Reaction #2055685

Reaction equation

4-Maleimidobutyric acid

tert-butyl hydrazinecarboxylate

EDC

→

title compound

Yield 85.0%

tert-Butyl 2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoyl)hydrazinecarboxylate

Yield 85.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with 1 M NaH2PO4
2. 2
   Drying/NaCl (conc), dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   Otherpurified on SiO2 chromatography
6. 6
   Washeluted with MeOH/DCM (1:25)

Procedure

4-Maleimidobutyric acid (245 mg, 1.33 mmol), tert-butyl hydrazinecarboxylate (201 mg, 1.52 mmol) and EDC (400 mg, 2.08 mmol) in 5 ml of CH2Cl2, were stirred overnight under Ar, washed with 1 M NaH2PO4,/NaCl (conc), dried over MgSO4, filtered, evaporated and purified on SiO2 chromatography eluted with MeOH/DCM (1:25) to afford 335 mg (85%) of the title compound. 1H NMR (CDCl3), 7.83 (br, 1H), 6.65 (s, 2H), 6.50 (br, 1H), 3.58 (t, 2H, J=6.3 Hz), 2.15 (t, 2H, J=7.0 Hz), 1.90 (dt, 2H, J=6.8, 13.4 Hz), 1.40 (s, 9H); 13C NMR 171.30, 155.61, 134.41, 82.00, 37.13, 31.38, 28.36, 24.95; MS m/z+ 320.2 (M+Na).

Source