Acetic Acid → HCID 59540281, compound

HRID 923433Notes

Reaction equation

HRID 923433 reaction equation
[CH2:1]([NH:3][C@H:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH3:2].[CH3:18][C:19]([CH3:21])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CCO>[CH2:1]([N:3]([CH:19]([CH3:21])[CH3:18])[C@H:4]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 59540229HCID 59540229, compound

Product 1

HCID 59540281HCID 59540281, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of product from example 122A (0.098 g, 0.416 mmol) in EtOH (5 mL) was added acetone (0.031 mL, 0.416 mmol), acetic acid (0.024 mL, 0.416 mmol), and sodium cyanoborohydride (0.039 g, 0.625 mmol), and the resulting mixture and stirred at rt for 8 hrs. The mixture was partitioned between CH2Cl2 and saturated aq. NaHCO3, and the organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-1% MeOH in CH2Cl2 to give the title compound (0.0352 g, 31%).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and saturated aq. NaHCO3
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-613b7e49fe114f73b25f801f9923c16d
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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