Water → HCID 24891203, compound

HRID 1798012Notes

Reaction equation

HRID 1798012 reaction equation
C(OC(=O)CNC[C:8]([C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9])C.[OH2:18].[OH-:19].[Na+]>C1COCC1.C(Cl)(Cl)Cl.C(O)(C)C>[OH:16][C:15]1[C:10]([C:8]([N:11]([CH2:10][C:8]([OH:19])=[O:18])[CH3:12])=[O:9])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67212343HCID 67212343, compound

Product 1

HCID 24891203HCID 24891203, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

To a solution of [(3-hydroxy-pyridine-2-carbonyl)methylamino]acetic acid ethyl ester, 32, (0.10 g, 0.42 mmol) in THF (4 mL) is added H2O (1 mL) and NaOH (0.90 g, 2.25 mmol). The reaction is stirred for 3 hours then concentrated under reduced pressure. The remaining oil is acidified to pH ˜1 with 1M HCl and the solution is concentrated under reduced pressure to give an off-white solid. The solid is suspended in CHCl3:isopropanol (1:1) then collected by filtration. The solid is washed with additional CHCl3:isopropanol (1:1) then transferred to a flask and triturated with Et2O to afford 0.075 g (85% yield) of the desired compound as a pale yellow solid. 1H NMR (250 MHz, MeOD) δ ppm (rotamers) 8.26 (1 H, br s), 7.63-7.74 (1 H, m), 7.56-7.63 (1 H, m), 4.38 (1 H, s), 4.32 (1 H, s), 3.20 (1.5 H, s), 3.12 (1.5 H, s). HPLC-MS: m/z 211 [M+H]+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. concentrationthe solution is concentrated under reduced pressure
  3. customto give an off-white solid
  4. filtrationthen collected by filtration
  5. washThe solid is washed with additional CHCl3:isopropanol (1:1)
  6. customthen transferred to a flask
  7. customtriturated with Et2O

Sources & evidence

ORD record
ord-83149d1d5cf244f9915a3e31c5fd4266
Source dataset
uspto-grants-2013_01
Patent number
US08343952B2

Reaction notes

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