Ethanol → HCID 178513659, compound

HRID 1625210Notes

Reaction equation

HRID 1625210 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:16]=[C:15]([N:17]3[C:21]4=[N:22][CH:23]=[CH:24][C:25]([C:26]5[CH:27]=[N:28][C:29]6[C:34]([CH:35]=5)=[CH:33][CH:32]=[CH:31][CH:30]=6)=[C:20]4[C:19]([C:36]([F:39])([F:38])[F:37])=[N:18]3)[CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH2:4][CH2:3]1.C([OH:42])C.[OH-].[Na+].OO>CS(C)=O.O.C(OCC)(=O)C>[OH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[CH:16]=[C:15]([N:17]3[C:21]4=[N:22][CH:23]=[CH:24][C:25]([C:26]5[CH:27]=[N:28][C:29]6[C:34]([CH:35]=5)=[CH:33][CH:32]=[CH:31][CH:30]=6)=[C:20]4[C:19]([C:36]([F:39])([F:38])[F:37])=[N:18]3)[CH:14]=[CH:13][C:10]=2[C:11]([NH2:12])=[O:42])[CH2:6][CH2:7]1

Participants

8

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178510018HCID 178510018, compound

Product 1

HCID 178513659HCID 178513659, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Compound (1f) (0.450 g) was dissolved in dimethyl sulfoxide (hereinafter referred to as DMSO, 2 mL) and ethanol (4 mL). An aqueous sodium hydroxide solution (4 M, 0.851 mL) and a 30% hydrogen peroxide solution (0.193 mL) were added to the resulting solution in this order at room temperature, followed by stirring for 30 min. Water was added to the reaction solution, the reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (1) (0.300 g, 65%) as a white solid.

Workup

  1. washthe organic layer was washed with saturated saline
  2. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away
  4. customThe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-eddd1e6bd28c454b8247f5c4d856e6b2
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

Loading…