Citric Acid → 4-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid

HRID 914361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914361
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([S:27][C:28]([CH3:36])([CH3:35])[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[S:25][CH:26]=2)[C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][N:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:31]([C:29](=[O:30])[C:28]([S:27][C:24]1[S:25][CH:26]=[C:22]([CH2:21][CH2:20][N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=2)[C:12]2[N:13]=[CH:14][C:15]([CH2:18][CH3:19])=[CH:16][N:17]=2)[N:23]=1)([CH3:35])[CH3:36])([CH3:32])([CH3:33])[CH3:34]

Komponenten

6

Edukt 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 673973504-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester

Produkt 1

HCID 673979184-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acidAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-{[(2-{2-[(2-tert-Butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester (2.2 g) synthesized in Example 437-1 was dissolved in methanol (50 mL) and tetrahydrofuran (50 mL), 1N aqueous sodium hydroxide solution (16 ml) was added, and the mixture was stirred at 60° C. for 4 hr. Aqueous 10% citric acid solution was added, and the mixture was extracted with chloroform. The insoluble material was filtered off, and the filtrate was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.0 g) as an oil.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. filtrationThe insoluble material was filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b2741d158073431cb141bd49fed25898
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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