Potassium Carbonate → 4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

HRID 337380Notes

Reaction equation

HRID 337380 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.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].O.C(O)(=O)[CH2:20][C:21]([CH2:26]C(O)=O)([C:23](O)=O)O>O>[C:21]([O:13][C:12]([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:15])([CH3:26])([CH3:23])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.00 g (13.2 mmol) of 4-(aminomethyl)benzoic acid suspended in water (20 ml) was mixed with 3.81 g (27.6 mmol) of potassium carbonate and then with 3.57 g (16.4 mmol) of di-tert-butyl bicarbonate under cooling with ice. The mixture was allowed to react at 40° C. for 2.5 hours and stirred at room temperature overnight. Then, water (7 ml) and 5.6 g of citric acid monohydrate were gradually added, and the precipitated solid was collected by filtration, washed with water and dried under reduced pressure to obtain the desired product (3.05 g, yield 92%).

Workup

  1. customto react at 40° C. for 2.5 hours
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b375890fd9a64dbaa50925d0741b2f15
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

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