Ethanol → HCID 136005817, compound

HRID 915925Notes

Reaction equation

HRID 915925 reaction equation
C(O)C.[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]5)=[CH:22][C:21]=4[O:33][CH3:34])=[N:14][C:13]=3[N:12]([CH3:35])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[BH4-].[Na+]>CC(C)=O>[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]5)=[CH:22][C:21]=4[O:33][CH3:34])=[N:14][C:13]=3[N:12]([CH3:35])[N:11]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 136005896HCID 136005896, compound

Product 1

HCID 136005817HCID 136005817, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 30 ml ethanol suspension of 780 mg (1.79 mmol) of the compound obtained in Example 30, 81 mg (2.15 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 1.5 hours. Then, acetone was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with methylene chloride. The organic layer was washed with water and a saturated aqueous solution of sodium chloride in this order. Then, the washed layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=40/1) to obtain 606 mg (77%) of the captioned compound.

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialThen, the washed layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol=40/1)

Sources & evidence

ORD record
ord-47a7a7af360a4ba6be6fb6fbe1a2bddf
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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