Phosphorus oxychloride → HCID 59168618, compound

HRID 444684Notes

Reaction equation

HRID 444684 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][CH:12]([CH2:17][OH:18])[CH2:13][CH2:14][CH2:15][CH3:16])=O)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)Cl>>[CH2:13]([CH:12]1[CH2:17][O:18][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:11]1)[CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59168651HCID 59168651, compound

Product 1

HCID 59168618HCID 59168618, compound

Procedure

Compound 978 (50 mg) was treated with POCl3 (1.0 mL). This was stirred overnight. The solvent was removed via reduced pressure distillation. The residue was washed with aqueous sodium bicarbonate and then dissolved in EtOAc. The solvent was dried, filtered and evaporated. The residue was dissolved in acetone (1 mL) and refluxed with water (2 mL) for 1.5 hrs. The solution was extracted with EtOAc, the organic layer evaporated and the residue chromatographed on silica to give the target compound. 1H NMR (300 MHz, CDCl3) δ=7.38 (s, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.05 (br, 1H), 7.00 (d, 7.5 Hz, 1H), 4.47 (m, 1H), 3.95 (m, 2H), 1.8-1.2 (m, 6H), 0.95 (m, 3H). ESIMS=224.9 m/z (M+H)

Workup

  1. customThe solvent was removed via reduced pressure distillation
  2. washThe residue was washed with aqueous sodium bicarbonate
  3. dissolutiondissolved in EtOAc
  4. customThe solvent was dried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in acetone (1 mL)
  8. temperaturerefluxed with water (2 mL) for 1.5 hrs
  9. extractionThe solution was extracted with EtOAc
  10. customthe organic layer evaporated
  11. customthe residue chromatographed on silica
  12. customto give the target compound

Sources & evidence

ORD record
ord-09061dfe9fe34c789dc32c296d8f09bd
Source dataset
uspto-grants-2013_07
Patent number
US08476043B2

Reaction notes

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