Lithium Hydroxide → HCID 69672843, compound

HRID 1751447Notes

Reaction equation

HRID 1751447 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([NH:12][C:13]([O:15][CH3:16])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)C.[Li+].[OH-]>C1COCC1.CO.C(Cl)Cl>[CH3:16][O:15][C:13]([NH:12][CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[C:4]([OH:17])=[O:3])=[O:14]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 69672065HCID 69672065, compound

Product 1

HCID 69672843HCID 69672843, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Methoxycarbonylamino-pyridin-2-yl-acetic acid ethyl ester (0.26 g, 1.1 mmol) in THF (6.0 mL) and MeOH (2.0 mL) was added aqueous LiOH (2.5 M, 2.2 mL, 5.5 mmol). The solution was stirred at room temperature for 1.5 h. The reaction was diluted with CH2Cl2 and washed with aqueous ammonium chloride and brine. The aqueous layers were combined and concentrated. The resulting solid was triterated with MeOH and filtered. The filtrated was concentrated and triterated a second time with MeOH. Concentration of the filtrate provided Methoxycarbonylamino-pyridin-2-yl-acetic acid which was used crude in the next step. LCMS-ESI+: calc'd for C9H10N2O4: 210.06 (M+); Found: 210.98 (M+H+).

Workup

  1. washwashed with aqueous ammonium chloride and brine
  2. concentrationconcentrated
  3. filtrationfiltered
  4. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-0107ab473385401081bfd44fd650efc7
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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