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

HRID 441193Notes

Reaction equation

HRID 441193 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 53.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Using a similar procedure to that of Example 1.d., above, 3-benzyloxycarbonylamino-6-methylpyrid-2-one (1.80 g) was added to a suspension of NaH (0.33 g) in dry dimethylformamide (50 mL). After the mixture had been stirred for 45 min, ethyl iodoacetate (1.48 g) 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 phase was washed with brine (twice), dried and evaporated. The resulting yellow, waxy solid was chromatographed, eluting with ethyl acetate:dichloromethane (3:97), to give ethyl (3-benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetate (1.28 g); TLC: Rf =0.52, dichloromethane:ethyl acetate (95:5); NMR: 1.21 (t,3, J=8.6), 2.26 (s,3), 4.16 (q,2, J=8.6), 4.84 (s,2), 5.15 (s,2), 6.20 (d,1, J=9), 7.32-7.43 (m,5), 7.76 (d,1, J=9), 8.38 (s,1); MS: m/z=345(M+1).

Workup

  1. stirringand the mixture was stirred overnight
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. washThe organic phase was washed with brine (twice),
  4. customdried
  5. customevaporated
  6. customThe resulting yellow, waxy solid was chromatographed
  7. washeluting with ethyl acetate:dichloromethane (3:97)

Sources & evidence

ORD record
ord-9b427d5e834446fea3eeb8dc525984d1
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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