Acetone → HCID 57859971, compound

HRID 1947127Notes

Reaction equation

HRID 1947127 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:20][C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]([CH2:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:11](=[O:30])[C:10]=2[C:9]=1[O:31][CH3:32])=[O:7].[CH3:33][C:34]([CH3:36])=O.CN(C=O)C.C([BH3-])#N.[Na+]>CO.C(=O)([O-])O.[Na+]>[CH3:32][O:31][C:9]1[C:10]2[C:11](=[O:30])[N:12]([CH2:21][C:22](=[O:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]=2[S:20][C:8]=1[C:6]([NH:5][CH2:4][CH2:3][NH:2][CH:34]([CH3:36])[CH3:33])=[O:7]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6228DimethylformamideHCID 5003444Sodium cyanoborohydrideHCID 66892788HCID 66892788, compound

Product 1

HCID 57859971HCID 57859971, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixed solution of the compound of Example 61 (150 mg, 0.32 mmol) and acetone (0.2 mL) in methanol (5 mL)-DMF (5 mL) was added sodium cyanoborohydride (20 mg, 0.32 mmol), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was combined, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate), and the obtained white solid was recrystallized from ethyl acetate-hexane to give the title compound (69 mg, 45%) as white crystals.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate)
  6. customthe obtained white solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7a8319aabaf748e19eb3150255a91844
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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