Hydrochloric Acid → 4-[2-(2-Hydroxy-4-methoxybenzoylamino)benzoylamino]butanoic acid

HRID 2374713

Reaktionsgleichung

Reaktionsgleichung von HRID 2374713
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5].C[Si](Cl)(C)C.C(N(CC)CC)C.[OH:29][C:30]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].[OH-].[Na+].Cl>C(Cl)Cl>[OH:29][C:30]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:31]=1[C:32]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5])=[O:33]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 134423754-(2-Aminobenzamido)butanoic acidHCID 231185592-Hydroxy-4-methoxybenzoyl chloride

Produkt 1

HCID 231185584-[2-(2-Hydroxy-4-methoxybenzoylamino)benzoylamino]butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 1.00 g (4.50 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 20 ml of dry methylene chloride, add 4.50 g (38.50 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 0.58 g (5.70 mmol) of triethylamine and a solution of 0.71 g (38.5 mmol) of 2-hydroxy-4-methoxybenzoyl chloride dissolved in 10 ml of dry methylene chloride. Allow the reaction to stir for 30 minutes in an ice bath and 24 hours at room temperature. Eliminate the solvent at low pressure, add 30 ml of 10% NaOH to the crude product and continue stirring the mixture until the oil has completely disappeared. Immediately acidify with concentrated HCl, filter the resulting solid and wash several times with water and with ether. Purify the reaction product by recrystallization (EtOH/H2O). This yields 0.54 g (38%) of 4-[2-(2-hydroxy-4-methoxybenzoylamino)benzoylamino]butanoic acid as a white solid.

Aufarbeitung

  1. customthe reaction
  2. temperatureto reflux for 5 hours
  3. customthe reaction
  4. stirringcontinue stirring the mixture until the oil
  5. filtrationfilter the resulting solid
  6. washwash several times with water
  7. customPurify the reaction product
  8. customby recrystallization (EtOH/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-4448cfeceb7444f8bff327f5cacad762
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462735B2

Verknüpfte Notizen

Wird geladen…