Tetrahydrofuran → 2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(2-thiazolyl)thio]-pentanoic Acid

HRID 1884276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884276
O1CCCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH:24]([CH2:29][CH:30]3[O:32][CH2:31]3)[C:25]([O:27]C)=[O:26])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.CCN(CC)CC.[SH:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1>C1C=CC=CC=1.O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([S:20]([NH:23][CH:24]([CH2:29][CH:30]([OH:32])[CH2:31][S:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12073922Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoateHCID 178527881HCID 178527881, Verbindung

Produkt 1

HCID 98919232-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(2-thiazolyl)thio]-pentanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-[2-oxo-5-(thiazol-2-yl)thio]methyl]-tetrahydrofuran: To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.7 g, 1.79 mmol) in benzene (5 mL) and Et3N (0.33 mL, 2.3 mmol) at room temperature is added slowly 2-mercaptothiazole (0.52 g, 4.48 mmol). The reaction mixture is stirred for 4 h at room temperature. The resulting mixture is diluted with water, and the mixture is then extracted three times with EtOAc. The combined EtOAc layer is consecutively washed with water, and brine, dried over MgSO4 and concentrated to an oil under reduced pressure. Purification is accomplished by column chromatography with hexane/EtOAc (4:1 to 7:3 to 6:4) eluent to give the desired product.

Aufarbeitung

  1. extractionthe mixture is then extracted three times with EtOAc
  2. washThe combined EtOAc layer is consecutively washed with water, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil under reduced pressure
  5. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-41a224d556ea4b4da3e5124b0273696d
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762198B2

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