Hydrochloric Acid → HCID 68984879, compound

HRID 2249646Notes

Reaction equation

HRID 2249646 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]O)[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].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl.C(Cl)Cl.O>[NH2:36][CH:17]([C:7]1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:11][C:6]=1[O:5][CH2:1][CH:2]([CH3:3])[CH3:4])[C:18]1[CH:19]=[CH:20][C:21]([O:31][CH2:32][CH:33]([CH3:34])[CH3:35])=[C:22]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86630047HCID 86630047, compound

Product 1

HCID 68984879HCID 68984879, compoundYield 85.2%

Reagents, catalysts & solvents 4

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

At 5° C., 5.56 g of nickel (II) chloride hexahydrate is added to a solution of 6.00 g of ethyl 3-{5-[(2,4-diisobutoxyphenyl)(hydroxyimino)methyl]-2-isobutoxyphenyl}propanoate in 60 ml of methanol. Then, 4.42 g of sodium borohydride is portionwise added over a period of one hour. Water is added to the reaction mixture, and then 6 mol/L hydrochloric acid is dropwise added and stirred at ambient temperature for 10 minutes. pH is adjusted to 9 with saturated aqueous solution of sodium bicarbonate, methylene chloride is added, 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. Thus, 4.97 g of ethyl 3-{5-[amino(2,4-diisobutoxyphenyl)methyl]-2-isobutoxyphenyl}propanoate is obtained as a brown oily product.

Workup

  1. additionis added
  2. customthe organic layer is separated
  3. customThe organic layer thus obtained
  4. washis washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-376e897819124946befbe4766e9a1ed3
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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