Ethylamine → Benzyl tert-butyl tetrahydropyridazine-1,2-dicarboxylate

HRID 1108792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108792
[C:1]([O:5][C:6](=[O:17])[C@H](CC1C=CC(F)=CC=1)N)([CH3:4])([CH3:3])[CH3:2].[CH2:18](N)[CH3:19].Cl[C:22]([O:24][C:25]1C=CC([N+]([O-])=O)=CC=1)=[O:23].Cl.Cl.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C(N([CH:48]([CH3:50])[CH3:49])CC)(C)C.[CH2:51](Cl)Cl>C(OCC)(=O)C>[C:6]([N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][N:37]1[C:22]([O:24][CH2:25][C:19]1[CH:18]=[CH:49][CH:48]=[CH:50][CH:51]=1)=[O:23])([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:17]

Komponenten

8

Edukt 6

HCID 6341EthylamineHCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 16059220tert-butyl (2S)-2-amino-3-(4-fluorophenyl)propanoateHCID 18784097Pyridazine dihydrochloride

Produkt 1

HCID 21186018Benzyl tert-butyl tetrahydropyridazine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.1 g (0.42 mmol) 4-fluorophenylalanine tert-butyl ester in 1.0 mL of CH2Cl2 at 0° C. was added 0.065 g (0.5 mmol) of dilsopropyl ethyl amine followed by 0.093 g (0.46 mmol) of p-nitrophenyl chloroformate as a solid. After 30 minutes a solution of 82.7 mg (0.52 mmol) of pyridazine dihydrochloride (Step C) and 0.2 g (1.56 mmol) of diisopropylethylamine in 1.5 mL of CH2Cl2 was added. The reaction mixture was stirred for 2.5 hours and diluted with 20 mL of ethyl acetate. The solution was washed with water twice followed by brine and was dried over MgSO4. The mixture was filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography eluting with 45% EtOAc/hexanes to provide the title compound. 1H-NMR (CDCl3, 400 MHz): 1.38 (s, 9H); 1.60 (b, 6H); 2.8 (b, 2H); 3.05 (m, 2H); 15 4.57 (m, 1H); 6.75 (b, 1H); 6.95 (m, 2H); 7.15 (m, 2H).

Aufarbeitung

  1. washThe solution was washed with water
  2. dry with materialwas dried over MgSO4
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash silica gel chromatography
  6. washeluting with 45% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a66663160810484cb4bdc283b60801f4
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06069163

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