Sodium Bicarbonate → 2'-(Benzyloxycarbonylaminomethyl)biphenyl-2-carboxylic acid

HRID 2109537Notes

Reaction equation

HRID 2109537 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:15]([OH:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1.[C:18](=[O:21])([O-])[OH:19].[Na+]>O1CCOCC1.O>[CH2:2]([O:19][C:18]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:15]([OH:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 155093832'-Aminomethylbiphenyl-2-carboxylic acid

Product 1

HCID 109153932'-(Benzyloxycarbonylaminomethyl)biphenyl-2-carboxylic acidYield 163.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

500 mg (2 mmol) of benzyl N-succinimidocarbonate dissolved in 2.5 ml of dioxane were added dropwise at 0° C. to a solution of 455 mg (2 mmol) of 2′-aminomethylbiphenyl-2-carboxylic acid (precursor 3) and 336 mg (4 mmol) of sodium hydrogencarbonate in 5 ml of dioxane and 5 ml of water. After stirring at RT for 4 h, the mixture was concentrated in vacuo, diluted with water, acidified and extracted with ethyl acetate. 590 mg of 2′-(benzyloxycarbonylaminomethyl)biphenyl-2-carboxylic acid were obtained.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-25e2fc8decb14d57a537d4895f320312
Source dataset
uspto-grants-2009_04
Patent number
US07514582B2

Reaction notes

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