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

HRID 358301

Reaction equation

HRID 358301 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:27]=1[CH2:28]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[N:18]([CH2:28][C:27]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:26]=2[O:25][CH3:24])[C:17]1=[O:22])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 817502,4-Dimethoxybenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13105389Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 100 ml of tetrahydrofuran were dissolved 3.2 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester, 1.8 g of 2,4-dimethoxybenzyl alcohol and 3.9 g of triphenylphosphine and under ice-cooling 2 ml of diethyl azodicarboxylate was added. The mixture was stirred at room temperature for one hour and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with 5% sodium hydrogen carbonate and 10% phosphoric acid in that order and dried over sodium sulfate. The solution was concentrated under reduced pressure and the concentrate was chromatographed on a silica gel column, elution being carried out with toluene-ethyl acetate (7:3). The eluate was concentrated under reduced pressure and to the residue was added petroleum ether. The precipitate was collected by filtration and dried. Yield 1.2 g.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with 5% sodium hydrogen carbonate and 10% phosphoric acid in that order
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe concentrate was chromatographed on a silica gel column, elution
  8. concentrationThe eluate was concentrated under reduced pressure and to the residue
  9. additionwas added petroleum ether
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-7f80ed19ce8148eea873befe7a1827be
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Linked notes

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