Benzyl Alcohol → HCID 21310889, compound

HRID 583313Notes

Reaction equation

HRID 583313 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[S:13]([C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1)(=[O:15])=[O:14].[CH2:31]([OH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[H-].[Na+]>CN(C=O)C>[CH2:23]([N:12]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:38][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:5]1[C:6]([CH3:11])=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=1[C:3]([OH:2])=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 15859214HCID 15859214, compound

Product 1

HCID 21310889HCID 21310889, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.50 g (1.171 mmol) of the product of Example 65 in 10 mL of DMF was added 0.485 mL (4.684 mmol) of benzyl alcohol and 0.187 g (4.684 mmol) of 60% sodium hydride. The eaction mixture was stirred for 18 h at room temperature and the quenched with 5% HCl solution. The resulting mixture was extracted with ether and the combined organics were washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved 10 mL of MeOH-THF (1:1) and 4.7 mL of 1N sodium hydroxide solution was added. The resulting mixture was heated to reflux for 18 h and then cooled to room temperature, acidified with 5% HCl and extracted with EtOAc. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. Triturion of the residue with edter provided 0.432 g (74%) of the desired product as a white solid. Electrospray Mass Spec: 502.3 (M+H)+.

Workup

  1. customthe quenched with 5% HCl solution
  2. extractionThe resulting mixture was extracted with ether
  3. washthe combined organics were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved 10 mL of MeOH-THF (1:1) and 4.7 mL of 1N sodium hydroxide solution
  8. additionwas added
  9. temperatureThe resulting mixture was heated
  10. temperatureto reflux for 18 h
  11. temperaturecooled to room temperature
  12. extractionextracted with EtOAc
  13. washThe combined organics were washed with water and brine
  14. dry with materialdried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27e32358e5b54f0fa38554054e491956
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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