Benzyl chloroformate → 4-((((Benzyloxy)carbonyl)amino)methyl)benzoic acid

HRID 1720798Notes

Reaction equation

HRID 1720798 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.[OH-].[Na+].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH2:14]([O:21][C:22]([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:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 14799974-((((Benzyloxy)carbonyl)amino)methyl)benzoic acidYield 22.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(aminomethyl)benzoic acid (25 g) in a 2N aqueous solution of sodium hydroxide (100 ml), a solution of benzyloxycarbonyl chloride (33.8 g) in tetrahydrofuran (50 ml) was added drop by drop under ice cooling conditions, followed by stirring at room temperature for 2 hours. The resulting precipitate was collected by filtration, washed with water, 1N hydrochloric acid and ether and dried under reduced pressure to yield the title compound (10.5 g, yield 22%) as a colorless powder.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water, 1N hydrochloric acid and ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-b64250adb0c64724b592c000a6d1ee2f
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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