Hydrochloric Acid → HCID 68989846, compound

HRID 2249623Notes

Reaction equation

HRID 2249623 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[C:15](=[O:33])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:18]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:17]=1)[C:9](O)=[O:10])[CH:2]([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.[CH:40]([NH2:43])([CH3:42])[CH3:41].Cl>C(Cl)Cl.O.C(OCC)(=O)C.CN(C)C=O>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15](=[O:33])[C:14]2[CH:13]=[CH:12][C:8]([C:9]([NH:43][CH:40]([CH3:42])[CH3:41])=[O:10])=[CH:7][C:6]=2[O:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[CH:17][C:18]=1[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:24]([CH3:26])[CH3:25]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 65578Oxalyl chlorideHCID 68984650HCID 68984650, compound

Product 1

HCID 68989846HCID 68989846, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 2.5 ml of methylene chloride is dissolved 0.25 g of 3-isobutoxy-4-[4-isobutoxy-3-(3-methoxy-3-oxopropyl)benzoyl]benzoic acid. At ambient temperature, 60 μl of oxalyl chloride is added and then 20 μl of N,N-dimethylformamide is added, and the mixture thus obtained is stirred at ambient temperature for one hour. The reaction mixture is cooled with ice water, 0.12 ml of isopropylamine is dropwise added thereto, and the mixture thus obtained is stirred at ambient temperature for one hour. Ethyl acetate and water are added to the reaction mixture, pH is adjusted to 2 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer 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 to obtain 0.12 g of methyl 3-(2-isobutoxy-5-{2-isobutoxy-4-[(isopropylamino)carbonyl]benzoyl}-phenyl)propanoate as a white solid product.

Workup

  1. customthe mixture thus obtained
  2. additionis dropwise added
  3. customthe mixture thus obtained
  4. stirringis stirred at ambient temperature for one hour
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f21933e632f4e7b8335ce48131681f9
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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