Water → HCID 59583407, compound

HRID 2170529Notes

Reaction equation

HRID 2170529 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]=[N+:9]=[N-:10].[C:17]([O:23][CH3:24])(=[O:22])[CH2:18][C:19]([CH3:21])=O.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:19]([CH3:21])=[C:18]([C:17]([O:23][CH3:24])=[O:22])[N:10]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 7757Methyl acetoacetateHCID 11430Potassium CarbonateHCID 19791786HCID 19791786, compound2×

Product 1

HCID 59583407HCID 59583407, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-biphenylylmethyl azide (Intermediate 2) (1.1 g, 5.2 mmol) and methyl acetoacetate (0.9 g, 7.8 mmol) in DMSO (10 mL) was added potassium carbonate (2.9 g, 20 mmol). The reaction mixture was stirred at 40° C. for 48 hours. After cooling, water was added and the mixture was extracted with ethyl acetate, the organic layer was dried on sodium sulphate and after filtration was evaporated to dryness. The residue was purified by flash column chromatography eluting with DCM and DCM/MeOH: 98/2 to give the title compound as an oil (1.1 g, 68.7%). LC/MS: m/z 308 (M+H)+, Rt: 3.14 min.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customthe organic layer was dried on sodium sulphate
  4. filtrationafter filtration
  5. customwas evaporated to dryness
  6. customThe residue was purified by flash column chromatography
  7. washeluting with DCM and DCM/MeOH

Sources & evidence

ORD record
ord-444660d6daef4613899cfbc3bc4db906
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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