Monobasic potassium phosphate → 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]leucinate

HRID 1744131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744131
[Br:1][C:2]1[C:3]([N:14](C(OCC(Cl)(Cl)Cl)=O)[C@H:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:4][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:6]=1.OP([O-])(O)=O.[K+]>C1COCC1.[Zn]>[Br:1][C:2]1[C:3]([NH:14][C@H:15]([C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:4][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH:6]=1

Komponenten

5

Edukt 2

HCID 516951Monobasic potassium phosphate2×HCID 691522654-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

Produkt 1

HCID 691517634-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]leucinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (2.38 g, 3.54 mmol) in THF (40 mL) was added activated zinc powder (2.3 g, 35.4 mmol) and an aqueous solution of KH2PO4 (1.0 M, 14.2 mL, 14.2 mmol) dropwise. After 1 hour additional aliquots of activated zinc powder (2.3 g, 35.4 mmol) and aqueous KH2PO4 solution were added (1.0 M, 14.2 mL, 14.2 mmol) and the reaction mixture was stirred for 1 hour. The zinc powder was filtered off, rinsed with Et2O and water and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 3/7) to afford 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]leucinate.

Aufarbeitung

  1. filtrationThe zinc powder was filtered off
  2. washrinsed with Et2O and water
  3. extractionthe product extracted with ether (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography over silica gel (EtOAc/Hex, 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-d754436a39ab46da8a70b8da1a7a30bd
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012075B2

Notizen zur Reaktion

Wird geladen…