Hydrochloric Acid → [(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid

HRID 1177994Notes

Reaction equation

HRID 1177994 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:23])[CH2:6][N:7]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10])[CH3:8].O.Cl>C1COCC1.CO.O>[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:16][C:11]([C:9]([N:7]([CH2:6][C:5]([OH:23])=[O:4])[CH3:8])=[O:10])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 43407419[(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester

Product 1

HCID 43239699[(Biphenyl-4-carbonyl)-methyl-amino]-acetic acidYield 84.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (293 mg, 6.9 mmol) was added to a stirred solution of [(biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester (330 mg, 1.1 mmol) in THF:MeOH:H2O (2:2:1, 10 mL), and the resulting mixture was stirred at room temperature for 4 hrs. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with 10% aqueous HCl, filtered the solid precipitated to afford 250 mg (79.7% yield) of [(biphenyl-4-carbonyl)-methyl-amino]-acetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. filtrationfiltered the solid
  4. customprecipitated

Sources & evidence

ORD record
ord-20a0eb0db1a94f569661b1567e984ef9
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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