HCID 67785949, compound → HCID 19391062, compound

HRID 1756695Notes

Reaction equation

HRID 1756695 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:14]=1[O:15]COC)[CH2:10][NH2:11].[CH3:23][S:24][C:25]1[CH:30]=[CH:29][C:28]([N:31](C2C=CC([N+]([O-])=O)=CC=2)[C:32](=O)[O-:33])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:8]=[C:9]([CH2:10][NH:11][C:32]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([S:24][CH3:23])=[CH:26][CH:27]=2)=[O:33])[CH:12]=[C:13]([C:19]([CH3:21])([CH3:20])[CH3:22])[C:14]=1[OH:15]

Participants

4

Reactant 2

HCID 67785949HCID 67785949, compoundHCID 67786136HCID 67786136, compound

Product 1

HCID 19391062HCID 19391062, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4.2 g (12.2 mmol) of the compound of Example 3 dissolved in 50 ml of toluene were added 3.70 g (12.2 mmol) of the compound of Example 12. The resulting solution was heated to reflux, stirred at that temperature for 45 minutes and then cooled to room temperature. Any solid particulates which had precipitated upon cooling were removed by filtration and the filtrate was concentrated to dryness to provide a residue. This residue was purified by column chromatography (10-40% ethyl acetate in hexane gradient as eluent) and fractions containing the desired product were combined and concentrated to dryness to provide 3.33 g of title compound.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customAny solid particulates which had precipitated
  4. temperatureupon cooling
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated to dryness
  7. customto provide a residue
  8. customThis residue was purified by column chromatography (10-40% ethyl acetate in hexane gradient as eluent) and fractions
  9. additioncontaining the desired product
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6e7dc42316f54c4b87ef7b4f33025a91
Source dataset
uspto-grants-1995_08
Patent number
US05441984

Reaction notes

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