Sodium hydride → ethyl 1-[2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionyl]cyclopentylcarboxylate

HRID 1274855Notes

Reaction equation

HRID 1274855 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:25])([CH3:24])[C:11](=[O:23])[CH:12]([CH2:18][CH2:19][CH2:20][CH2:21]I)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:26])[C:5]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH3:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:25])([CH3:24])[C:11]([C:12]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:23])[C:6](=[O:26])[C:5]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22118288HCID 22118288, compound

Product 1

HCID 22118305ethyl 1-[2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionyl]cyclopentylcarboxylateYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (40 mg of 60% oil dispersion) was added at 0° C. to a solution of ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-(4'-iodobutyl)-4-methyl-3-oxo-pentanoate (0.25 g) in N,N-dimethylformamide, and stirred at 20° C. for 2 hours. The mixture was diluted (ether),washed (brine), dried (MgSO4) and evaporated. The residue was purified by column chromatography (ethyl acetate/hexane 1:3) to give ethyl 1-[2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionyl]cyclopentylcarboxylate (Compound 1, 0.14 g), NMR 1.21(3H, t), 1.4-1.6(8H, m), 1.7-1.8(2H, m), 1.91(3H, s), 2.1-2.2(2H, m), 2.4-2.5(2H, m), 3.60(2H, s), 4.14(2H, q), 5.16(2H, s), 7.2-7.4(5H, m).

Workup

  1. dry with materialdried (MgSO4)
  2. customevaporated
  3. customThe residue was purified by column chromatography (ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-9edbe19983804321b029f31e083f99d8
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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