Hydrochloric Acid → HCID 86630048, compound

HRID 2249644Notes

Reaction equation

HRID 2249644 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:7]=1[C:17](=[N:36][OH:37])[C:18]1[CH:19]=[CH:20][C:21]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[C:22]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=1)[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:41][C:42]([NH2:44])=[O:43].Cl>CN(C)C=O.O.C(OCC)(=O)C>[NH2:44][C:42](=[O:43])[CH2:41][O:37][N:36]=[C:17]([C:7]1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:11][C:6]=1[O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[C:18]1[CH:19]=[CH:20][C:21]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[C:22]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 86630047HCID 86630047, compound

Product 1

HCID 86630048HCID 86630048, compoundYield 49.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 5 ml of N,N-dimethylformamide is dissolved 2.0 g of ethyl 3-{5-[(2,4-diisobutoxyphenyl)-(hydroxyimino)methyl]-2-isobutoxyphenyl}propanoate, to which is added 0.19 g of 60% sodium hydride. The mixture thus obtained is stirred at ambient temperature for 30 minutes. Then, 1.07 g of 2-bromoacetamide is added and the mixture thus obtained is stirred at ambient temperature for one hour and further at 80° C. for 15 minutes. The reaction mixture is added to a mixture of ethyl acetate 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 1.09 g of ethyl 3-{5-[[(2-amino-2-oxoethoxy)imino](2,4-diisobutoxyphenyl)methyl]-2-isobutoxyphenyl}propanoate as a colorless oily product.

Workup

  1. customThe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred at ambient temperature for one hour and further at 80° C. for 15 minutes
  4. customthe organic layer is separated
  5. customThe organic layer thus obtained
  6. washis 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
  9. customThe residue thus obtained
  10. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7b80bb4d89194e05a3990433e2b917b6
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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