Methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate → 2-(4-(4-(3-(2-Chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

HRID 1024450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024450
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:33])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([C:22]([NH:24][CH:25]([CH:30]([CH3:32])[CH3:31])[C:26]([O:28]C)=[O:27])=[O:23])[S:20][CH:21]=2)=[CH:13][CH:12]=1>C1COCC1.O.[OH-].[Li+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:33])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([C:22]([NH:24][CH:25]([CH:30]([CH3:31])[CH3:32])[C:26]([OH:28])=[O:27])=[O:23])[S:20][CH:21]=2)=[CH:13][CH:12]=1

Komponenten

4

Edukt 1

HCID 52934823Methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Produkt 1

HCID 529348242-(4-(4-(3-(2-Chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 168937Lithium hydroxide, monohydrateLösungsmittel

Versuchsvorschrift

To methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 23, 120 mg) in THF (2 ml), 1N lithium hydroxide monohydrate (1.2 ml) was added and reaction mixture was stirred for 16 hours at RT. Organic solvent was concentrated and added water, dilute HCl was added under stirring to pH acidic. The reaction mixture was filtered, and the residue was washed by water, and dried. The residue was dissolved in acetone, pet ether was added, solid was filtered and dried obtain title compound as solid. Yield: 70 mg (60%). 1H NMR (DMSO-d6, 300 MHz): δ 12.98 (bs, 1H), 9.59 (s, 1H), 8.48 (d, 1H), 8.35 (s, 1H), 8.30 (s, 1H), 8.17 (d, 1H), 8.03 (d, 2H), 7.58 (d, 2H), 7.46 (d, 1H), 7.30 (t, 1H), 7.02 (t, 1H), 4.33 (s, 1H), 2.26 (s, 1H), 0.98 (d, 6H).

Aufarbeitung

  1. customreaction mixture
  2. concentrationOrganic solvent was concentrated
  3. additionadded water, dilute HCl
  4. additionwas added
  5. stirringunder stirring
  6. filtrationThe reaction mixture was filtered
  7. washthe residue was washed by water
  8. customdried
  9. dissolutionThe residue was dissolved in acetone
  10. additionpet ether was added
  11. filtrationsolid was filtered
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d226652f6d66410e9adf069bd05ca6d9
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

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