Acetone → HCID 69437508, compound

HRID 1890650Notes

Reaction equation

HRID 1890650 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[CH3:29][C:30]([CH3:32])=O.C([BH3-])#N.[Na+].O>C(O)C.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH:30]([CH3:32])[CH3:29])[CH2:25][CH2:24]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 23156185HCID 23156185, compound

Product 1

HCID 69437508HCID 69437508, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of Compound 143 (0.150 g, 0.40 mmol) in ethanol was added with acetone (0.029 mL, 0.40 mmol) and titanium tetraisopropoxide (0.149 mL, 0.50 mmol). After 1 hour, the mixture was added with sodium cyanoborohydride (17 mg, 0.27 mmol) followed by stirring at room temperature overnight. The reaction mixture was added with water and extracted with chloroform three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:2 mol/L ammonia-methanol solution=19:1). The obtained crystals were recrystallized from ethanol-diisopropyl ether to obtain Compound 156 (21.5 mg, 0.051 mmol, 13%).

Workup

  1. extractionextracted with chloroform three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform:2 mol/L ammonia-methanol solution=19:1)
  5. customThe obtained crystals were recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-563316fa80f4490ba247f8984fca2619
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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