Methanol → [(5-Phenyl-pyridine-2-carbonyl)-amino]-acetic acid

HRID 1093624Notes

Reaction equation

HRID 1093624 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][N:10]=1)=[O:8])C.CO.O.O[Li].O>C1COCC1>[C:15]1([C:12]2[CH:13]=[CH:14][C:9]([C:7]([NH:6][CH2:5][C:4]([OH:21])=[O:3])=[O:8])=[N:10][CH:11]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66591735[(5-Phenyl-pyridine-2-carbonyl)-amino]-acetic acid ethyl ester

Product 1

HCID 57874442[(5-Phenyl-pyridine-2-carbonyl)-amino]-acetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-phenyl-pyridine-2-carboxylic acid (0.3 g, 0.00151 mol) in DMF (5 mL) was added DIPEA (0.580 g, 0.00452 mol), HOBt (0.243 g, 0.00180 7 mol) and EDCI.HCl (0.346 g, 0.001807 mol) at ambient temperature. After 2 minutes glycine ethyl ester hydrochloride (0.252 g, 0.00181 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.32 g (75%) of [(5-phenyl-pyridine-2-carbonyl)-amino]-acetic acid ethyl ester. To a stirred solution of [(5-phenyl-pyridine-2-carbonyl)-amino]-acetic acid ethyl ester (0.32 g, 0.00113 mol) in a mixture of THF (3.2 mL), methanol (2 mL) and H2O (1 mL) was added LiOH.H2O (0.142 g, 0.00338 mol) and the resulting mixture was stirred at ambient temperature overnight. Volatiles were removed by evaporation and the resulting residue was diluted with water and acidified with 10% HCl. The product was extracted with ethyl acetate, which was dried over sodium sulfate and concentrated under reduced pressure to afford 0.24 g (83%) of [(5-phenyl-pyridine-2-carbonyl)-amino]-acetic acid.

Workup

  1. customVolatiles were removed by evaporation
  2. additionthe resulting residue was diluted with water
  3. extractionThe product was extracted with ethyl acetate, which
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec532bd221214e0893db879e7cada927
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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