Potassium Carbonate → HCID 86667781, compound

HRID 1484487Notes

Reaction equation

HRID 1484487 reaction equation
[N:1]([CH:4]([O:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)[CH2:5][CH2:6][CH2:7][NH:8]C(=O)C(F)(F)F)=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:8][CH2:7][CH2:6][CH2:5][CH:4]([N:1]=[N+:2]=[N-:3])[O:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86667780HCID 86667780, compound

Product 1

HCID 86667781HCID 86667781, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 4-[(1-azido-4-trifluoroacetamidobutoxy)methyl]benzoate (0.4 g; 1.1 mmol) in MeOH (4.6 mL) was added a solution of potassium carbonate (0.4 g; 2.9 mmol) in water (2.4 mL) and stirred at room temperature for 4 h. The mixture was diluted with water and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography (MeCN+5% MeOH) to provide methyl 4-[(4-amino-1-azidobutoxy)methyl]benzoate in 0.19 g yield (65%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltrated
  4. customevaporated
  5. customThe residue was purified by column chromatography (MeCN+5% MeOH)

Sources & evidence

ORD record
ord-06f133502a8f435eafe746ccb3fbc2aa
Source dataset
uspto-grants-2016_08
Patent number
US09422232B2

Reaction notes

Loading…