Hydrochloric Acid → [(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid

HRID 1430198Notes

Reaction equation

HRID 1430198 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)=[O:7].O.O[Li].O.Cl>C1COCC1>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:21])=[O:2])=[O:7])[CH:13]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 24891097[(4-(4-Methylphenyl)pyridine-2-carbonyl)amino]-acetic acid methyl ester

Product 1

HCID 24891149[(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acidYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(4-(4-methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 24, (0.092 g, 0.32 mmol) in THF (2 mL) at room temperature is added H2O (1 mL) and LiOH.H2O (0.027 g, 0.64 mmol). The reaction is stirred for 16 hours after which time the solution is acidified using 1M HCl. The solvents are removed under reduced pressure and the solid that remains is suspended in a mixture of THF: MeOH and filtered. The filtrate is concentrated under reduced pressure and the resulting solid is triturated with MeOH and collected by filtration to provide 0.012 g (12% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, MeOD) δ ppm 8.69 (1H, d, J=4.8 Hz), 8.38 (1H, s), 7.86 (1H, d, J=6.2 Hz), 7.72 (2H, d, J=8.1 Hz), 7.38 (1H, d, J=7.9 Hz), 4.21 (1H, s), 2.44 (2H, s). HPLC-MS: m/z 271 [M+H]+.

Workup

  1. customThe solvents are removed under reduced pressure
  2. additionthe solid that remains is suspended in a mixture of THF
  3. filtrationMeOH and filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe resulting solid is triturated with MeOH
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-638d5ebb0aba476bbfd7456dd4301f9f
Source dataset
uspto-grants-2015_01
Patent number
US08940773B2

Reaction notes

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