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

HRID 849288Notes

Reaction equation

HRID 849288 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>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:19])[N:14]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

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, waxy 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, waxy solid was chromatographed
  6. washeluting with 3% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-85d7f701c718478c962f46660dd350d8
Source dataset
uspto-grants-2000_01
Patent number
US06011158

Reaction notes

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