Ethyl iodoacetate → Ethyl 6-methyl-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1(2H)-pyridineacetate

HRID 2257100Notes

Reaction equation

HRID 2257100 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:19])[NH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O.Cl>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:14]1[C:15]([CH3:18])=[CH:16][CH:17]=[C:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C:13]1=[O:19])[CH3:28]

Participants

6

Reactant 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 100838403-benzyloxycarbonylamino-6-methyl-2-pyridinone

Product 1

HCID 18323889Ethyl 6-methyl-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1(2H)-pyridineacetateYield 55.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The compound of Example 13 (1.80 g, 7.0 mmole) was added to a stirred suspension of sodium hydride (0.33 g, 8.4 mmole) in dry dimethylformamide (50 mL). After 45 minutes, ethyl iodoacetate (1.43 g, 6.7 mmole) was added, and the mixture was stirred overnight, diluted with 10% hydrochloric acid (300 mL) and extracted with ethyl acetate (3×150 mL). The organic layer was washed with brine (twice), dried and evaporated. The resulting yellow, wary solid was chromatographed, eluting with 3% ethyl acetate in dichloromethane, to give the title compound (1.28 g, 53% yield). Rf =0.52 (silica gel, 5:95 methanol:dichloromethane). Fast atom bombardment mass spectrometry confirmed the theoretical molecular weight of 344.

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe organic layer was washed with brine (twice),
  3. customdried
  4. customevaporated
  5. customThe resulting yellow, wary solid was chromatographed
  6. washeluting with 3% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-d1f2a6517ce64604936485f1c05e87ef
Source dataset
uspto-grants-1997_08
Patent number
US05656645

Reaction notes

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