Water → HCID 22118293, compound

HRID 1274862Notes

Reaction equation

HRID 1274862 reaction equation
Br[CH:2]([CH3:24])[CH2:3][CH2:4][C:5](=[O:23])[C:6]([N:9]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([CH3:22])[O:11][CH2:10]1)([CH3:8])[CH3:7].C([O-])(=[O:27])C.[Na+].O>CN(C)C=O>[CH3:22][C:12]1[O:11][CH2:10][N:9]([C:6]([CH3:8])([C:5](=[O:23])[CH2:4][CH2:3][CH:2]([OH:27])[CH3:24])[CH3:7])[C:14](=[O:15])[C:13]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 517045Sodium AcetateHCID 22118296HCID 22118296, compound

Product 1

HCID 22118293HCID 22118293, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-bromo-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylheptan-3-one (1.04 g), sodium acetate (0.43 g) and water (0.10 g) in N,N-dimethylformamide was heated at 70° C. for 2 hours. Water was added and the mixture extracted (dichloromethane) and the organic phase dried (magnesium sulphate) and evaporated. The residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate (3:1), to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-3-oxo-heptan-6-ol (Compound 212, 0.22 g) as a brown gum, NMR 1.2(d,3H), 1.4(2s,6H), 1.6(m,1H), 1.9(m,2H), 1.9(s,3H), 2.5(m,1H), 2.8(m,1H), 3.8(m,1H), 5.3(m,2H), 7.3(m,5H).

Workup

  1. extractionthe mixture extracted (dichloromethane)
  2. dry with materialthe organic phase dried (magnesium sulphate)
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-36872ad6fe99416a8c4e353ca2bcf998
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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