Water → HCID 18360085, compound

HRID 2081974Notes

Reaction equation

HRID 2081974 reaction equation
CNC1C=CC(C(N[C@H](C(OCC)=O)CCC(OCC)=O)=O)=NC=1.[C:25]([O:29][C:30]([N:32]([C:34]1[CH:35]=[CH:36][C:37]([C:40]([O:42]C)=[O:41])=[N:38][CH:39]=1)[CH3:33])=[O:31])([CH3:28])([CH3:27])[CH3:26].CI.O>C(O)C>[C:25]([O:29][C:30]([N:32]([C:34]1[CH:35]=[CH:36][C:37]([C:40]([OH:42])=[O:41])=[N:38][CH:39]=1)[CH3:33])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 19779302HCID 19779302, compoundHCID 54458760HCID 54458760, compound

Product 1

HCID 18360085HCID 18360085, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Note (6): Diethyl N-[5-(methylamino)picolinoyl]-L-glutamate used as starting material was prepared as follows:-A mixture of methyl 5-(N-tert-butoxycarbonyl-N-methylamino)picolinate (prepared using the method described in the Journal of Medicinal Chemistry, 1980, 23, 1405 except that methyl iodide was used in place of 3-trifluoromethylbenzyl chloride; 1.13 g), aqueous N-sodium hydroxide solution (8.5 ml), water (21 ml) and ethanol (15 ml) was stirred at laboratory temperature for 16 hours. The mixture was concentrated to a volume of 5 ml, acidified to pH 4 with 2N-hydrochloric acid solution and extracted with ethyl acetate (2×40 ml). The combined extracts were dried over magnesium sulphate, filtered and evaporated to give 5-(N-tert-butoxycarbonyl-N-methylamino)picolinic acid (0.8 g).

Workup

  1. customwas prepared
  2. customprepared
  3. concentrationThe mixture was concentrated to a volume of 5 ml
  4. extractionextracted with ethyl acetate (2×40 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-08052d06f47f4254b481ed8a6d70269e
Source dataset
uspto-grants-1993_02
Patent number
US05187167

Reaction notes

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