Sodium Hydroxide → 2-[(4-{2-[(5-Carboxy-3-chloropyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914415
[C:1]([O:5][C:6](=[O:37])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26]2[C:31]([Cl:32])=[CH:30][C:29]([C:33]([O:35]C)=[O:34])=[CH:28][N:27]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:37])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26]2[C:31]([Cl:32])=[CH:30][C:29]([C:33]([OH:35])=[O:34])=[CH:28][N:27]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:8])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 597592482-[(4-{2-[(3-Chloro-5-methoxycarbonylpyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Produkt 1

HCID 673985452-[(4-{2-[(5-Carboxy-3-chloropyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl esterAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-[(4-{2-[[3-Chloro-5-(methoxycarbonyl)pyridin-2-yl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (2.50 g) obtained in Example 281-1 was dissolved in ethanol (25 mL), 1N aqueous sodium hydroxide solution (5 mL) was added, and the mixture was left standing for 12 hr. The reaction mixture was concentrated, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=50:1) to give 2-[(4-{2-[(5-carboxy-3-chloropyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (2.5 g) as a colorless oil. Without purification, the present compound was dissolved in dichloromethane (20 mL), WSCD (0.72 g) and ammonia/methanol solution (7M, 1 mL) was added, and the mixture was stirred at room temperature for 12 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:2) to give the title compound (0.86 g) as a colorless oil.

Aufarbeitung

  1. waitthe mixture was left
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-25be55a73b434a5ebb8da4176937206f
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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