4-Methylmorpholine → {(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

HRID 1158505

Reaktionsgleichung

Reaktionsgleichung von HRID 1158505
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[Br:47][C:48]1[CH:56]=[CH:55][C:51]([CH2:52][NH:53][NH2:54])=[CH:50][CH:49]=1>CCOC(C)=O>[CH2:4]([O:3][C:1](=[O:2])[NH:11][C@H:12]([C:16]([NH:54][NH:53][CH2:52][C:51]1[CH:55]=[CH:56][C:48]([Br:47])=[CH:49][CH:50]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 167731114-Bromobenzylhydrazine

Produkt 1

HCID 11532141{(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl esterAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Cbz-(L)-Valine (1.04 g, 4.14 mmol) was dissolved in EtOAc (50 mL) and EDAC (0.870 g, 4.54 mmol), HOBT (0.610 g, 4.51 mmol), and NMM (0.500 mL, 4.55 mmol) were added. The reaction mixture was stirred at room temperature for 30 min and then 4-bromo-benzylhydrazine (1.00 g, 4.97 mmol) in EtOAc (5 mL) was added and the stirring was continued for 2 h. After evaporation of the solvent, CHCl3 was added and the solution was washed with saturated NaHCO3 (aq.) and brine followed by drying (Na2SO4), filtration and evaporation of the organic solvent. The crude product was purified by column chromatography (silica, CHCl3/MeOH, 100:0-95:5) yielding the title compound (1.42 g, 79%) as a white solid.

Aufarbeitung

  1. waitthe stirring was continued for 2 h
  2. customAfter evaporation of the solvent, CHCl3
  3. additionwas added
  4. washthe solution was washed with saturated NaHCO3 (aq.) and brine
  5. customby drying
  6. filtration(Na2SO4), filtration and evaporation of the organic solvent
  7. customThe crude product was purified by column chromatography (silica, CHCl3/MeOH, 100:0-95:5)

Quellen und Nachweise

ORD-Eintrag
ord-0df577dc0a4546529ac95ddd46b4284f
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807677B2

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