Lithium Hydroxide → 2-Thiophenecarboxylic acid, 3-[cyclopropyl(2,4-dichlorobenzoyl)amino]-5-phenyl-

HRID 2193924

Reaktionsgleichung

Reaktionsgleichung von HRID 2193924
C[O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[N:10]([CH:21]1[CH2:23][CH2:22]1)[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[CH:21]1([N:10]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:9]2[CH:8]=[C:7]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])[CH2:23][CH2:22]1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 207757633-[Cyclopropyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 160748072-Thiophenecarboxylic acid, 3-[cyclopropyl(2,4-dichlorobenzoyl)amino]-5-phenyl-Ausbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

3-[Cyclopropyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (85 mg, 0.19 mmol) was dissolved in a mixture of THF-MeOH—H2O (3:2:1) (10 mL) and then 1.2 ml of LiOH 1N was added to it. After 60 min of stirring at room temperature, solvent was removed and then partitioned between 15 ml of H2O, 4 ml of KHSO4 5% and 15 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (10% MeOH/CH2Cl2) to obtain 22 mg (27%) of 3-[Cyclopropyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid. NMR 1H (DMSO, 400 MHz): rotamer: 7.75 ppm (m, 2H, Haro); 7.68 ppm (m Haro, minor rotamer); 7.62-7.55 ppm (m, 2H, Haro); 7.52 ppm (m, Haro, minor rotamer); 7.48-7.27 ppm (m, 5H, Haro); 3.14 ppm (m, minor rotamer); 3.04 ppm (m, 1H, major rotamer); 0.87-0.42 ppm (m, 4H).

Aufarbeitung

  1. customsolvent was removed
  2. custompartitioned between 15 ml of H2O, 4 ml of KHSO4 5% and 15 ml of EtOAc
  3. customThe organic layer was separated
  4. washthe aqueous phase was washed twice with ethyl acetate (2×10 mL)
  5. dry with materialThe combined ethyl acetate layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was purified by preparative chromatography (10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-bcd76d9f3f50416a89ad516d62f5d81d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329924B2

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