Hydrochloric Acid → HCID 23118563, compound

HRID 2374717Notes

Reaction equation

HRID 2374717 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:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[C:32]([OH:39])[CH:31]=1.[OH-].[Na+].Cl>C(Cl)Cl>[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:1][C:2]2[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5])=[O:35])=[C:32]([OH:39])[CH:31]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 129247084-Chloro-2-hydroxybenzoyl chlorideHCID 134423754-(2-Aminobenzamido)butanoic acid

Product 1

HCID 23118563HCID 23118563, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2.00 g (9.00 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 40 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 (11.50 mmol) of triethylamine and a solution of 1.45 g (7.70 mmol) of 4-chloro-2-hydroxybenzoyl 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, filter the resulting solid and wash several times with water and ether. Purify the reaction product by recrystallization (EtOH/H2O). This yields 1.35 g (47%) of 4-[2-(4-chloro-2-hydroxybenzoylamino)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 and ether
  7. customPurify the reaction product
  8. customby recrystallization (EtOH/H2O)

Sources & evidence

ORD record
ord-72fb1ab5f02b45608b2ff42911df13d8
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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