Water → HCID 117830903, compound

HRID 515892Notes

Reaction equation

HRID 515892 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C@H:20]([CH2:21][CH2:22][C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=O)[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>CC(OC)(C)C.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C@H:20]([CH2:21][CH2:22][CH2:23][N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117830931HCID 117830931, compound

Product 1

HCID 117830903HCID 117830903, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a solution of 6.0 g (14.0 mmol) of the compound obtained in Step D in 60 mL of MTBE and 14 mL of dichloromethane there are added 1.06 g (28 mmol) of LAH in portions over 5 minutes. The batch is stirred at ambient temperature for 15 hours. There are added, dropwise, 1.5 mL of water and stirring is carried out for 15 minutes. There are then added, dropwise, 1.5 mL of 5M sodium hydroxide solution and stirring is carried out for 15 minutes. The reaction mixture is then diluted with MTBE and dichloromethane. The suspension is then filtered and the precipitate is washed with MTBE and dichloromethane. The organic phase is then dried over MgSO4, filtered and concentrated to dryness. After purification by chromatography over silica gel using dichloromethane and ammonia-in-ethanol as eluants, the expected product is obtained in the form of an oil.

Workup

  1. additionThere are added
  2. waitis carried out for 15 minutes
  3. additionThere are then added
  4. waitis carried out for 15 minutes
  5. filtrationThe suspension is then filtered
  6. washthe precipitate is washed with MTBE and dichloromethane
  7. dry with materialThe organic phase is then dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customAfter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-54478c3395044068a52ce6929f5209a8
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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