Hydrochloric Acid → (+/-)-{3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetic acid

HRID 2305229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305229
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=4)[C:28]([NH:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].O.Cl>O1CCCC1.CO.O>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=4)[C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 9892894HCID 9892894, Verbindung

Produkt 1

HCID 9913581(+/-)-{3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of ethyl (±)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetate (136.8 mg, 0.263 mmol) in tetrahydrofuran (4 ml) was added a solution of lithium hydroxide-water (22.1 mg, 0.526 mmol) in MeOH-water (1:1) (2.8 ml) at 5° C. and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1N-hydrochloric acid (0.8 ml) at 5° C. and extracted with EtOAc. The organic layer was washed with water and brine successively, dried over magnesium sulfate, and evaporated in vacuo to give (±)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetic acid (129.0 mg, 100%).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-25bd1906430e49c681eb0b5ddbe753bf
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06437146B1

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