Benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl ester → 2-[1-(2,4-Dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl]glycine methyl ester

HRID 358302Notes

Reaction equation

HRID 358302 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[C:17]1=[O:33])[NH:5]C(OCC1C=CC=CC=1)=O.[H][H]>CO.C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:34])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[C:17]1=[O:33])[NH2:5]

Participants

6

Reactant 2

HCID 20449787Benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 131053912-[1-(2,4-Dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl]glycine methyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

In a mixture of 50 ml of methanol and 5 ml of acetic acid was dissolved 3 g of benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl ester and after addition of 500 mg of palladium black, the mixture was stirred in a stream of hydrogen at room temperature for 2.5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness under reduced pressure. The concentrate was chromatographed on a silica gel column and eluted with toluene-acetone (4:1). The eluate was concentrated under reduced pressure and to the residue was added 100 ml of ethyl ether-petroleum ether (1:5). The mixture was allowed to stand in a refrigerator overnight and the resulting precipitate was collected by filtration and dried. Yield 1.4 g.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. customThe concentrate was chromatographed on a silica gel column
  4. washeluted with toluene-acetone (4:1)
  5. concentrationThe eluate was concentrated under reduced pressure and to the residue
  6. additionwas added 100 ml of ethyl ether-petroleum ether (1:5)
  7. customto stand in a refrigerator overnight
  8. filtrationthe resulting precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-27fdaffa258440a1b21492a9758932dc
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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