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

HRID 1968503Notes

Reaction equation

HRID 1968503 reaction equation
[C:1]1(=[O:13])[N:5]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[C:4](=[O:12])[CH:3]=[CH:2]1.[NH:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15].C(Cl)CCl>C(Cl)Cl>[O:13]=[C:1]1[CH:2]=[CH:3][C:4](=[O:12])[N:5]1[CH2:6][CH2:7][CH2:8][C:9]([NH:15][NH:14][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:11]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 70091tert-Butyl carbazateHCID 34049044-Maleimidobutyric Acid

Product 1

HCID 86644087tert-Butyl 2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoyl)hydrazinecarboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. washwashed with 1 M NaH2PO4
  2. dry with material/NaCl (conc), dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. custompurified on SiO2 chromatography
  6. washeluted with MeOH/DCM (1:25)

Sources & evidence

ORD record
ord-2d7c0d5a662f443eb47662ebcf7ca99e
Source dataset
uspto-grants-2013_04
Patent number
US08426402B2

Reaction notes

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