Sodium hydride → HCID 10095881, compound

HRID 441175Notes

Reaction equation

HRID 441175 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:26])[NH:14][C:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:26])[N:14]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:15]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 10043335HCID 10043335, compound

Product 1

HCID 10095881HCID 10095881, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Using a similar procedure to that of Example 1.d., above, 3-benzyloxycarbonylamino-6-phenethylpyrid-2-one (1.64 g) was suspended in dry dimethylformamide (20 mL) and to this suspension was added NaH (0.22 g of a 60% mineral oil dispersion). The mixture was stirred for 1.5 h, at which point all solids were in solution. tert-Butyl bromoacetate (0.92 g) was added, and the mixture was stirred overnight. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (four times). The extracts were washed with brine, dried and evaporated. The residue was purified by chromatography, eluting with methanol:dichloromethane (0:100 then 3:97), to give tert-butyl (3-benzyloxycarbonylamino-2-oxo-6-phenethyl-1,2-dihydro-1-pyridyl)acetate (0.578 g); TLC: Rf =0.17, dichloromethane; MS: m/z=463(M+1).

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with ethyl acetate (four times)
  3. washThe extracts were washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography
  7. washeluting with methanol:dichloromethane (0:100

Sources & evidence

ORD record
ord-01f35137252d4537805898a7e439db5d
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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