Citric Acid → HCID 75203050, compound

HRID 1519143Notes

Reaction equation

HRID 1519143 reaction equation
C([N:8]1[C:12]([NH:13][C:14]2C=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2CCC(O)=O)=[CH:11][N:10]=[N:9]1)C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].C(O)(=O)[CH2:31][C:32]([CH2:37][C:38](O)=O)([C:34]([OH:36])=[O:35])O.[C:43]1(C)C=CC=CC=1>O.CCOC(C)=O>[N:10]1[NH:9][N:8]=[C:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][C:38]=2[CH2:37][C:32]([CH3:31])([CH3:43])[C:34]([OH:36])=[O:35])[CH:11]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 86724062HCID 86724062, compound

Product 1

HCID 75203050HCID 75203050, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(2-((1-benzyl-1H-1,2,3-triazol-5-yl)amino)-5-chlorophenyl)propanoic acid 7h (85 mg, 0.22 mmol) in toluene (3.5 mL) was added aluminium trichloride (165 mg, 1.24 mmol) and the mixture heated at 100° C. for 1 h. The mixture was allowed to cool to room temperature and diluted with water and EtOAc followed by 5% citric acid solution. The aqueous was further extracted with EtOAc and the combined organics washed with brine, dried (MgSO4), and concentrated. Material was purified by ISCO (0-60% EtOAc/hexanes) to afford the title compound I-33 as an off white solid (36 mg, 38%). 1H NMR (500 MHz, d6-DMSO) δ 14.14 (1H, brs), 12.37 (1H, brs), 7.84 (1H, brs), 7.60-7.63 (1H, m), 7.38-7.41 (1H, m), 7.14 (1H, d), 7.08 (1H, d), 2.77 (1H, d), 2.67 (1H, d), 1.12 (6H, s). MS m/z: 295.1 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous was further extracted with EtOAc
  3. washthe combined organics washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customMaterial was purified by ISCO (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4f013f214826490fb016884920a7631d
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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