Hydrochloric Acid → HCID 11484643, compound

HRID 2374704Notes

Reaction equation

HRID 2374704 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.C([O:32][C:33]1[C:34](=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:35](Cl)=[O:36])(=O)C.[OH-].[Na+].Cl>C(Cl)Cl>[OH:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([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:36]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 796682-Acetoxybenzoyl chlorideHCID 134423754-(2-Aminobenzamido)butanoic acid

Product 1

HCID 11484643HCID 11484643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 20.36 g (91.71 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 200 ml of dry methylene chloride, add 42.33 g (391.92 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 11.87 g (117.57 mmol) of triethylamine and a solution of 15.52 g (78.38 mmol) of acetylsalicyloyl chloride dissolved in 20 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 200 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 21.66 g (81%) of 4-[2-(2-hydroxy-benzoylamino)benzoylamino]butanoic acid as a white solid.

Workup

  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)

Sources & evidence

ORD record
ord-18e92d89290d4896bd4540fb47774074
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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