HCID 21866933, compound → HCID 21866875, compound

HRID 857237Notes

Reaction equation

HRID 857237 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]1([CH3:25])[C:13]([C:18]([NH:20][CH2:21][CH:22]([OH:24])[CH3:23])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1>ClCCl>[C:12]1([CH3:25])[C:13]([C:18]([NH:20][CH2:21][C:22](=[O:24])[CH3:23])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21866933HCID 21866933, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 21866875HCID 21866875, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (15.91 g) was added to 143 ml of a suspension of 7.13 g of 1-(o-toluoylamino)-2-propanol and 15.91 g of celite in dichloromethane with stirring. The mixture was stirred for 4 hours at room temperature. The reaction solution was purified by silica gel column chromatography (Wakogel® C-200, chloroform) and the solvent was distilled off under reduced pressure. The eluate was purified again by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=1:2) to provide 5.73 g of the objective compound as colorless crystals. M.p. 65-66° C.

Workup

  1. stirringThe mixture was stirred for 4 hours at room temperature
  2. customThe reaction solution was purified by silica gel column chromatography (Wakogel® C-200, chloroform)
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe eluate was purified again by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=1:2)

Sources & evidence

ORD record
ord-f3c1297ee7444674847081556d690378
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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