Hydrochloric Acid → 4-[2-(3-Chlorobenzoylamino)benzoylamino]butanoic acid

HRID 2374721Notes

Reaction equation

HRID 2374721 reaction equation
[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:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34].[OH-].[Na+].Cl>C(Cl)Cl>[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([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:34]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 69252Benzoyl chloride, 3-chloro-HCID 134423754-(2-Aminobenzamido)butanoic acid

Product 1

HCID 231185714-[2-(3-Chlorobenzoylamino)benzoylamino]butanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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 3-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 0.83 g (30%) of 4-[2-(3-chlorobenzoylamino)benzoylamino]butanoic acid as a cream-coloured solid.

Workup

  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)

Sources & evidence

ORD record
ord-0c1b15872e704eca9cda830353ec906a
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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