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Sodium Hydroxide → HCID 59909759, Verbindung

HRID 2183034
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2183034
[CH2:1]([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:31])=[C:25]([C:27]([O:29]C)=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:31])=[C:25]([C:27]([OH:29])=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 59909776HCID 59909776, Verbindung

Produkt 1

HCID 59909759HCID 59909759, VerbindungAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazole-4-carboxylate (Preparation 71) (1.00 g, 2.26 mmol) in 1,4-dioxane (10 ml) was treated with an aqueous sodium hydroxide solution (1N, 1.5 ml) and stirred at room temperature for 4 hours. Further aqueous sodium hydroxide (1N, 3.0 ml) was added and the mixture was stirred for 20 hours. The solvent was removed under reduced pressure and the residue was dissolved in water and washed with ethyl acetate. The layers were separated and the aqueous layer was acidified with solid citric acid then extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulphate, filtered and the solvent was removed under reduced pressure to afford the title compound as a white foam (0.83 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 20 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washwashed with ethyl acetate
  5. customThe layers were separated
  6. extractionthen extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fad36a25ea094edc8ea20029ce4168cc
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06897306B2

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