4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

HRID 1978360Notes

Reaction equation

HRID 1978360 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml (100 mM) of 1M borane-THF complex was added 25.13 g (100 mM) of 4-[N-(tert-butoxycarbonyl)aminomethyl]benzoic acid at 0° C. and the mixture was stirred at room temperature for 1.5 hours. The reaction was stopped by adding iced water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure and the resulting crystal crop was harvested by filtration and rinsed with hexane to provide the title compound as white crystals.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was then distilled off under reduced pressure
  5. filtrationthe resulting crystal crop was harvested by filtration
  6. washrinsed with hexane

Sources & evidence

ORD record
ord-cb859b45d68f4a7ca7ed295a51eacf84
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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