Pyridine → Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine 2,2,2-trichloroethyl ester

HRID 358303Notes

Reaction equation

HRID 358303 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.ClC(O[CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=O>O1CCCC1>[Cl:35][C:34]([Cl:37])([Cl:36])[CH2:33][O:14][C:13](=[O:15])[CH:12]([CH:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 13105388Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

Product 1

HCID 20449783Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine 2,2,2-trichloroethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of tetrahydrofuran was dissolved 6.2 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine and, following addition of 1.2 ml of pyridine, a solution of 5.4 g of 2,2,2-trichloroethyl chloroformate in 30 ml of tetrahydrofuran was added dropwise under cooling at 0°-5° C. The reaction mixture was stirred at the same temperature as above for 30 minutes and under reflux for 5 minutes and then concentrated to dryness under reduced pressure. The residue was extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The concentrate was chromatographed on a silica gel column and eluted with toluene-ethyl acetate (3:1). The eluate was concentrated under reduced pressure, and the residue was dissolved in a small amount of ethyl ether. After addition of petroleum ether to the solution, the mixture was allowed to stand in a refrigerator overnight to give crystals. Yield 1.1 g.

Workup

  1. temperatureunder cooling at 0°-5° C
  2. temperatureunder reflux for 5 minutes
  3. concentrationconcentrated to dryness under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was chromatographed on a silica gel column
  9. washeluted with toluene-ethyl acetate (3:1)
  10. concentrationThe eluate was concentrated under reduced pressure
  11. dissolutionthe residue was dissolved in a small amount of ethyl ether
  12. additionAfter addition of petroleum ether to the solution
  13. customto stand in a refrigerator overnight
  14. customto give crystals

Sources & evidence

ORD record
ord-33d972500aa2477bb7ffc92fc71062ec
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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