HCID 19348504, compound → HCID 19348735, compound

HRID 1418229Notes

Reaction equation

HRID 1418229 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:34])[CH2:15][CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[C:23]=1[O:32][CH3:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:34])[CH2:15][CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[C:23]=1[O:32][CH3:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 19348504HCID 19348504, compound

Product 1

HCID 19348735HCID 19348735, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

31.0 g of mangenese dioxide were added to a solution of 3.10 g (6.57 mmol) of N-[2-t-butyl-5-(hydroxymethyl)phenyl]-3-(2,3,4-trimethoxyphenyl)octanamide (prepared as described in Preparation 68A) in 60 ml of chloroform, and the resulting mixture was stirred for 1.5 hours. At the end of this time, the reaction mixture was filtered using a Celite (trade mark) filter aid, and the manganese dioxide used was thoroughly washed with methylene chloride. The filtrate and the washings were combined and concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 2.68 g (yield 87%) of the title compound as a foam-like substance.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. filtrationfilter aid
  3. washthe manganese dioxide used was thoroughly washed with methylene chloride
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-e43b4302858c448685fe2d76553d5ece
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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