Lithium Hydroxide → (+/-)-3-Phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoic acid

HRID 989903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989903
[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 11189784Ethyl (+/-)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate

Produkt 1

HCID 9822714(+/-)-3-Phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoic acidAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of ethyl (±)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate (131 mg, 0.30 mmole) in 1:1 THF/H2O (10 mL) was added 1N LiOH (0.36 mL, 0.36 mmole). After 18 hr, the mixture was concentrated under reduced pressure. The residue was dissolved in 20 mL H2O then acidified to pH 6 using 10% HCl. The resulting cloudy solution was extracted with CH2Cl2 (3×75 mL). The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was triturated with Et2O to give the title compound as a white solid (63 mg, 51%) which was collected by filtration. MS (ES) m/e 409 (M+H)+. Anal. Calcd for C22H24N4O4.0.75 H2O, 1.5 HCl: C, 55.44; H, 5.71; N, 11.75. Found: C, 55.49; H, 5.54; N, 11.63.

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 20 mL H2O
  3. extractionThe resulting cloudy solution was extracted with CH2Cl2 (3×75 mL)
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-ca24fea2bb4e4459ae00c78152da7b25
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458814B1

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