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

HRID 2374719

Reaktionsgleichung

Reaktionsgleichung von HRID 2374719
[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.[Cl:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].[OH-].[Na+].Cl>C(Cl)Cl>[Cl:29][C:30]1[CH:38]=[CH:37][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 691102-Chlorobenzoyl chlorideHCID 134423754-(2-Aminobenzamido)butanoic acid

Produkt 1

HCID 231185644-[2-(2-Chlorobenzoylamino)benzoylamino]butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 2.00 g (9.01 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 20 mL of dry methylene chloride, add 8.36 g (77.00 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 1.17 g (11.55 mmol) of triethylamine and a solution of 1.35 g (7.70 mmol) of 2-chlorobenzoyl chloride dissolved in 5 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 and extract several times with ethyl acetate. Dry the organic phase with MgSO4 anhydrous and eliminate at low pressure. Wash the crude product several times with ether and finally, purify by recrystallization (EtOH/H2O). This yields 1.27 g (36%) of 4-[2-(2-chlorobenzoylamino)benzoylamino]butanoic acid as a brown solid.

Aufarbeitung

  1. customthe reaction
  2. temperatureto reflux for 5 hours
  3. customthe reaction
  4. stirringcontinue stirring the mixture until the oil
  5. extractionextract several times with ethyl acetate
  6. dry with materialDry the organic phase with MgSO4 anhydrous
  7. washWash the crude product several times with ether
  8. customfinally, purify by recrystallization (EtOH/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-deb66748c80c4cb08482d6a424814c9e
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462735B2

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