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Sodium Hydroxide → N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine

HRID 844847
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 844847
C[O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:33])[N:25]([CH3:32])[C:26](=[O:31])[N:27]([CH3:30])[C:28]=2[CH3:29])=[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:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:15])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:34])=[O:2])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24](=[O:33])[N:25]([CH3:32])[C:26](=[O:31])[N:27]([CH3:30])[C:28]=2[CH3:29])=[CH:21][CH:22]=1)=[O:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 69336733N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester

Produkt 1

HCID 69337248N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
47.5 °C

Versuchsvorschrift

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (2.2 mmol, 1.11 g) in ethanol (12 mL) was added aqueous 1.0 N sodium hydroxide (8.8 mL) at room temperature. The mixture was heated to 45-50° C. and the resulting clear solution was stirred for approximately 2 h. The ethanol was removed under reduced pressure and the residue was diluted with water (50 mL) and NaOH (5 mL, 1.0N) to dissolve the sodium salt. 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 into ethyl acetate (2×75 mL). The combined organic extracts were washed with brine solution (100 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate afforded 970 mg (90% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as a white solid: mp 225-227° C. FAB-HRMS m/e calcd for C23H21Cl2N3O5 (M+H) 490.0937, found 490.0940.

Aufarbeitung

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (50 mL) and NaOH (5 mL, 1.0N)
  3. dissolutionto dissolve the sodium salt
  4. washThe aqueous solution was washed with diethyl ether (50 mL)
  5. customto remove any neutral impurities
  6. extractionthe product was extracted into ethyl acetate (2×75 mL)
  7. washThe combined organic extracts were washed with brine solution (100 mL)
  8. dry with materialwere dried over anhydrous magnesium sulfate
  9. filtrationFiltration of the drying agent and concentration of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-71889abe14264981ac43c85b5415cff9
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06380387B1

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