HCID 178420399, compound → HCID 21272317, compound

HRID 1193513Notes

Reaction equation

HRID 1193513 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:17]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>ClCCl.[O-2].[O-2].[Mn+4]>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:20]=[CH:19][N:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:17]=3)=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 178420399HCID 178420399, compound

Product 1

HCID 21272317HCID 21272317, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (2.5 g) was added portionwise over 10-15 minutes to a solution of the product of step (a) (3.43 g) in dichloromethane (300 ml) stirred at room temperature. After stirring for an additional 30 minutes at room temperature, the reaction mixture was filtered, solvent was removed and the resulting gum was chromatographed on silica gel eluting with dichloromethane: ethyl acetate (95:5) to give the title compound (2.45 g) mp 145°-146°.

Workup

  1. stirringAfter stirring for an additional 30 minutes at room temperature
  2. filtrationthe reaction mixture was filtered
  3. customsolvent was removed
  4. customthe resulting gum was chromatographed on silica gel eluting with dichloromethane: ethyl acetate (95:5)

Sources & evidence

ORD record
ord-ac7534edc187413e95640ad8bfcc40d5
Source dataset
uspto-grants-1989_03
Patent number
US04810719

Reaction notes

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