Hydrochloric Acid → HCID 68983961, compound

HRID 2249641Notes

Reaction equation

HRID 2249641 reaction equation
[CH2:1]([O:5][C:6]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH:27]=[CH:26][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:14]([CH2:16][CH2:17][C:18](O)=[O:19])[CH:15]=1)=[O:9])[CH:2]([CH3:4])[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:47][S:48]([NH2:51])(=[O:50])=[O:49].N12CCCN=C1CCCCC2.Cl>O1CCCC1.O.C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH:27]=[CH:26][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:14]([CH2:16][CH2:17][C:18]([NH:51][S:48]([CH3:47])(=[O:50])=[O:49])=[O:19])[CH:15]=1)=[O:9])[CH:2]([CH3:4])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57684398HCID 57684398, compound

Product 1

HCID 68983961HCID 68983961, compoundYield 94.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran is dissolved 1.00 g of 3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]-propanoic acid, to which is added 0.52 g of 1,1′-carbonyldiimidazole at ambient temperature. The mixture thus obtained is heated under reflux for one hour with stirring. To the reaction mixture cooled to ambient temperature are added 0.22 g of methane-sulfonamide and 0.4 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene, and the mixture thus obtained is stirred for 30 minutes at ambient temperature. The reaction mixture is added to a mixture of chloroform and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1) to obtain 1.10 g of N-{3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoyl}methanesulfonamide as a white-colored foaming product.

Workup

  1. customThe mixture thus obtained
  2. temperatureis heated
  3. temperatureunder reflux for one hour
  4. customthe mixture thus obtained
  5. stirringis stirred for 30 minutes at ambient temperature
  6. customthe organic layer is separated
  7. customThe organic layer thus obtained
  8. washis washed with water and saturated aqueous solution of sodium chloride successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. customThe residue thus obtained
  12. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8e697479f02c4e989ffd2114f2164548
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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