Sodium Hydroxide → RO-0505376

HRID 895920

Reaktionsgleichung

Reaktionsgleichung von HRID 895920
C[O:2][C:3](=[O:36])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:35])[N:25]([CH3:34])[C:26]([CH3:33])=[CH:27][C:28]=2[C:29]([F:32])([F:31])[F:30])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])=[O:7].[OH-].[Na+]>C(O)C>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:36])=[O:2])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24](=[O:35])[N:25]([CH3:34])[C:26]([CH3:33])=[CH:27][C:28]=2[C:29]([F:31])([F:32])[F:30])=[CH:21][CH:22]=1)=[O:7]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 69714407N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester

Produkt 1

HCID 9806910RO-0505376Ausbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester (177 mg, 0.326 mmol) in ethanol (6 mL) was added 1N aqueous sodium hydroxide solution (4 mL) at room temperature. The mixture was stirred for 5 h. Then, the ethanol was removed under vacuum and the residue was diluted with water (20 mL). The aqueous solution was washed with diethyl ether (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine solution (50 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration afforded 159 mg (92% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine as a white solid: mp 238-240° C. ES-HRMS m/e calcd for C24H19Cl2F3N2O4 (M+Na) 549.0567. found 549.0570.

Aufarbeitung

  1. customThen, the ethanol was removed under vacuum
  2. additionthe residue was diluted with water (20 mL)
  3. washThe aqueous solution was washed with diethyl ether (50 mL)
  4. customto remove any neutral impurities
  5. extractionthe product was extracted with ethyl acetate (2×50 mL)
  6. washThe combined organic extracts were washed with brine solution (50 mL)
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. filtrationFiltration of the drying agent and concentration

Quellen und Nachweise

ORD-Eintrag
ord-95d1307f9f4a42ceaddcf50aa0a21712
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916933B2

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