Water → 2-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester

HRID 889275

Reaction equation

HRID 889275 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:5]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10980693Methyl 2-{4-[(tert-butoxycarbonyl)amino]butoxy}-6-hydroxybenzoate

Product 1

HCID 684315912-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-tert-butoxycarbonylamino-butoxy)-6-hydroxy-benzoic acid methyl ester (1.5 g, 4.4 mmol) in 20 mL of DMF is added benzyl bromide (0.56 mL, 4.6 mmol) and K2CO3 (1.8 g, 13.0 mmol) and the suspension is stirred at RT for 3 h. The mixture is poured into water and extracted with EtOAc. The organic layer is dried, filtered, and the solvent is removed under reduced pressure to give an oil that is purified by flash chromatography using a gradient of hexane/EtOAc (5:1 to 1:1) to give the product as a colorless liquid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure
  5. customto give an oil that
  6. customis purified by flash chromatography

Sources & evidence

ORD record
ord-92499a21116742afae35fc075768c6cb
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Linked notes

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