Hydrochloric Acid → 4-((((Benzyloxy)carbonyl)amino)methyl)benzoic acid

HRID 11862

Reaction equation

HRID 11862 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>[OH-].[Na+]>[C:20]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 14799974-((((Benzyloxy)carbonyl)amino)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

Commercially available 4-aminomethylbenzoic acid (5 g) was dissolved in 1 mol/l aqueous solution of sodium hydroxide (33 ml). Benzylchloroformate (5.2 ml) and 1 mol/l aqueous solution sodium hydroxide (40 ml) were gradually and simultaneously added while stirring at room temperature. After 3 hours, 1 mol/l hydrochloric acid was added to the reaction solution to adjust the pH to 3, and the deposited precipitate was collected by filtration through glass filter G4. The precipitate was washed with water and hexane, and dried under reduced pressure to obtain the title compound (8.162 g) as a white solid.

Workup

  1. additionsimultaneously added
  2. filtrationthe deposited precipitate was collected by filtration through glass
  3. filtrationfilter G4
  4. washThe precipitate was washed with water and hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-4d0b5681f2aa4659be4d853e461c318f
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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