Benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate → 2-(1,3-Dioxaindan-5-yl)propanoic acid

HRID 1533276Notes

Reaction equation

HRID 1533276 reaction equation
C(OC(N1C=C([CH2:13][CH:14]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[C:15]([O:17]CC2C=CC=CC=2)=[O:16])N=C1CCCC)=O)(C)(C)C>[Pd].CO.O>[CH2:32]1[O:31][C:28]2[CH:29]=[CH:30][C:25]([CH:14]([CH3:13])[C:15]([OH:17])=[O:16])=[CH:26][C:27]=2[O:33]1

Participants

5

Reactant 1

HCID 22012330Benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate

Product 1

HCID 183996542-(1,3-Dioxaindan-5-yl)propanoic acidYield 188%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of benzyl (2RS)-3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate (2R:2S=1:4, 3.65 g) and 10% palladium on activated carbon (1.0 g) in methanol (50 ml) and water (5 ml) was shaken under hydrogen atmosphere (3 atmospheric pressure) at ambient temperature for 1 hour. The catalyst was filtered through a bed of celite and the filtrate was evaporated in vacuo. The residue was diluted with AcOEt (ethyl acetate) and the organic layer was washed with brine. Drying, filtering and removal of the solvents afforded (2RS)-3-(1-tert-butoxycarbonyl)-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionic acid (2R:2S=1:4) (2.63 g) as a white solid.

Workup

  1. filtrationThe catalyst was filtered through a bed of celite
  2. customthe filtrate was evaporated in vacuo
  3. additionThe residue was diluted with AcOEt (ethyl acetate)
  4. washthe organic layer was washed with brine
  5. customDrying
  6. filtrationfiltering
  7. customremoval of the solvents

Sources & evidence

ORD record
ord-7bf5e29694da456099a778d606975bd5
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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