Sodium Hydroxide → HCID 57595392, Verbindung

HRID 1786067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786067
C([O:4][CH2:5][C:6]([N:8]([C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33]C)=[O:32])=[CH:23][CH:22]=2)=[O:20])[C@@H:11]([CH3:37])[CH2:10]1)=[O:7])(=O)C.[OH-].[Na+]>CO.O1CCCC1.O>[Cl:44][C:41]1[CH:40]=[CH:39][C:38]([N:8]([C:6](=[O:7])[CH2:5][OH:4])[C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([OH:33])=[O:32])=[CH:23][CH:22]=3)=[O:20])[C@@H:11]([CH3:37])[CH2:10]2)=[CH:43][CH:42]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 57595487HCID 57595487, Verbindung

Produkt 1

HCID 57595392HCID 57595392, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Methyl 5-(4-{[(2S,4R)-4-[[(acetyloxy)acetyl](4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (100 mg, 0.16 mmol, 1 eq.) was dissolved in methanol/tetrahydrofuran (2/1) (2 ml). A solution of sodium hydroxide (32 mg, 0.81 mmol, 5 eq.) in water (1 ml) was added and reaction mixture heated to 45° C. for 8 h and at room temperature for 20 h. The mixture was concentrated and the residue was acidified with a 1N HCl aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the crude acid. Purification by silica gel chromatography gave pure 5-(4-{[(2S,4R)-4-[(4-chlorophenyl)(glycoloyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoic acid (63 mg, 70%).

Aufarbeitung

  1. customreaction mixture
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude acid
  9. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4d8f0399fab14d8e912a54031e081cba
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504508B2

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