Water → HCID 12148502, compound

HRID 2216290Notes

Reaction equation

HRID 2216290 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:18])([CH3:17])[CH2:11][C:12](=[O:16])[C:13]([OH:15])=O)[C:4]=2[O:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[C:32](=[O:33])[O:31][N:30]=[C:29]([CH2:34]C)[C:28]=2[CH:36]=1.O>CC(N(C)C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:18])([CH3:17])[CH2:11][C:12](=[O:16])[C:13]([NH:23][C:24]3[CH:25]=[CH:26][C:27]4[C:32](=[O:33])[O:31][N:30]=[C:29]([CH3:34])[C:28]=4[CH:36]=3)=[O:15])[C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 21941648HCID 21941648, compoundHCID 21941653HCID 21941653, compound

Product 1

HCID 12148502HCID 12148502, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

10 g of 4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-pentanoic acid is dissolved in 125 ml of dimethylacetamide and mixed with 3.5 ml of thionyl chloride under argon at −0° C. After 20 minutes of stirring at −3 to +3° C., 7.6 g of 6-amino-4-ethyl-2,3-benzoxazin-1-one (WO00/32584) is added. It is stirred for 96 hours at room temperature, then mixed with water, extracted with ethyl acetate, the organic phase is washed with water, dried (Na2SO4), and after the solvent is concentrated by evaporation and after chromatography of the crude product on silica gel with hexane/ethyl acetate (100:0→60:40), 6.56 g of 6-[4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one is obtained as a beige solid.

Workup

  1. stirringIt is stirred for 96 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationafter the solvent is concentrated by evaporation

Sources & evidence

ORD record
ord-9a6f0036930c49c79c0dc72d8577c5e4
Source dataset
uspto-grants-2006_09
Patent number
US07112584B2

Reaction notes

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