Acetic Acid → HCID 11579350, compound

HRID 1200138Notes

Reaction equation

HRID 1200138 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:25])[CH2:12][CH2:13][NH:14]C(OCC1C=CC=CC=1)=O)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.O.[H][H]>CO.[Pd]>[CH3:9][C:2]([NH:10][C:11](=[O:25])[CH2:12][CH2:13][NH2:14])([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14696290HCID 14696290, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11579350HCID 11579350, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.5 g of palladium-on-carbon were suspended in a solution of 4.51 g of N-(α,α-dimethylbenzyl)-3-(benzyloxycarbonylamino)propionamide (prepared as described in Preparation 2) in 110 ml of an 8:2:1 by volume mixture in methanol, acetic acid and water, and then hydrogen was passed through the solution for 4 hours at room temperature under normal atmospheric pressure. Undissolved materials were filtered off, the pH was adjusted to a value of 10 by the addition of a 10% w/v aqueous solution of sodium hydroxide, and then the mixture was extracted with 150 ml of ethyl acetate. The solution was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure to give 2.3 g of the title compound as an oil.

Workup

  1. filtrationUndissolved materials were filtered off
  2. additionthe pH was adjusted to a value of 10 by the addition of a 10% w/v aqueous solution of sodium hydroxide
  3. extractionthe mixture was extracted with 150 ml of ethyl acetate
  4. washThe solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d56740fb26f14fc8960819b67f4037de
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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