Hydrochloric Acid → HCID 23118561, compound

HRID 2374703Notes

Reaction equation

HRID 2374703 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12])=[O:6].[OH:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].CCN(CC)CC.[OH-].[Na+].Cl>C(OCC)(=O)C>[OH:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:6])=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 74041Salicyloyl chlorideHCID 23118568HCID 23118568, compound

Product 1

HCID 23118561HCID 23118561, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2.60 g (11.00 mmol) of methyl 4-(3-aminobenzoylamino)butanoate dissolved in 25 ml of ethyl acetate, very slowly add 1.40 g (10.00 mmol) of 2-hydroxybenzoyl chloride dissolved in 5 ml of ethyl acetate. Then add 1.00 g (10.00 mmol) of Et3N (triethylamine) and keep the reaction mixture at room temperature for 24 hours. Eliminate the solvent at low pressure, add 40 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. Purify the reaction product by recrystallization (EtOH/H2O). This yields 1.60 g (48%) of 4-[3-(2-hydroxybenzoylamino) benzoylamino]butanoic acid as a white solid.

Workup

  1. customat room temperature
  2. customfor 24 hours
  3. filtrationfilter the resulting solid
  4. washwash several times with water
  5. customPurify the reaction product
  6. customby recrystallization (EtOH/H2O)

Sources & evidence

ORD record
ord-dd1190c868fb41df8d8aada6ed27099b
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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