HCID 58380065, compound → HCID 57467667, compound

HRID 404316Notes

Reaction equation

HRID 404316 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]2[CH2:15][CH:16](C(OC)=O)[C:17](=[O:18])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CS(C)=O.O>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]2[CH2:15][CH2:16][C:17](=[O:18])[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58380065HCID 58380065, compound

Product 1

HCID 57467667HCID 57467667, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

Compound H6.4 (2.50 g, 8.41 mmol) was dissolved in 27 mL DMSO and 3 mL water. The resulting mixture was heated to 150° C. and stirred for 30 minutes. After the reaction was complete, the reaction was diluted with 120 mL water and extracted twice with 50 mL EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated onto silica gel. The resulting product was purified by column chromatography with 10% EtOAc/hexane to afford desired product H6.5 (1.76 g, 87.5%). MS ESI (pos.) m/e: 240.1 (M+H)+.

Workup

  1. extractionextracted twice with 50 mL EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated onto silica gel
  5. customThe resulting product was purified by column chromatography with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-97effbf76feb4edba5f26e099bad2fc8
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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