Rac.-2-acetamido-3-[4-((1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester → Rac.-2-acetamido-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid

HRID 1647062Notes

Reaction equation

HRID 1647062 reaction equation
C([O:8][C:9](=[O:29])[CH:10]([NH:25][C:26](=[O:28])[CH3:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][CH:13]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:26]([NH:25][CH:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:17]=1)[C:9]([OH:29])=[O:8])(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 14888682Rac.-2-acetamido-3-[4-((1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14888687Rac.-2-acetamido-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acidYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of rac.-2-acetamido-3-[4-[(1,1-dimethyl-ethoxy)carbonyl]phenyl]propanoic acid benzyl ester (3.3 g, 8 mmol) and 10% Pd/C (320 mg) in ethanol (100 mL) was blanketed with hydrogen (1 atm) at room temperature. Upon the consumption of 1 equivalent of hydrogen, the mixture was filtered through celite. The celite pad was washed with ethanol (50 mL) and the filtrates were combined and concentrated. The resultant solid was purified by recrystallization from ethyl acetate/hexane to give rac.-2-acetamido-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid, (2.3 g, 7.4 mmol) in 89% yield, mp. 187°-188° C.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washThe celite pad was washed with ethanol (50 mL)
  3. concentrationconcentrated
  4. customThe resultant solid was purified by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a92d138d91d24cfaacb3c77e60430bde
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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