Benzyl Alcohol → Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine benzyl ester

HRID 358305Notes

Reaction equation

HRID 358305 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.[CH2:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:23]([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])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 13105388Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

Product 1

HCID 20449792Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 100 ml of tetrahydrofuran were dissolved 4.6 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine and 2.5 ml of benzyl alcohol, and under cooling at 0°-5° C. 2.4 ml of pyridine and 3.6 g of dicyclohexylcarbodiimide were added to the solution in that order. The mixture was stirred at the same temperature as above for 4 hours and then at room temperature for 18 hours. The precipitated dicyclohexylurea were filtered off and the filtrate was concentrated under reduced pressure. The residue was poured into a mixture of 300 ml of 2 N hydrochloric acid and 300 ml of ethyl acetate. The ethyl acetate layer was separated, washed with 2 N hydrochloric acid, 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. To this solution was added petroleum ether to give crystals. Yield 4.8 g.

Workup

  1. temperatureunder cooling at 0°-5° C
  2. waitat room temperature for 18 hours
  3. filtrationThe precipitated dicyclohexylurea were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe residue was poured into a mixture of 300 ml of 2 N hydrochloric acid and 300 ml of ethyl acetate
  6. customThe ethyl acetate layer was separated
  7. washwashed with 2 N hydrochloric acid
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrate was chromatographed on a silica gel column
  11. washeluted with toluene-ethyl acetate (3:1)
  12. concentrationThe eluate was concentrated under reduced pressure
  13. dissolutionthe residue was dissolved in a small amount of ethyl ether
  14. additionTo this solution was added petroleum ether
  15. customto give crystals

Sources & evidence

ORD record
ord-3184261f4fd94892b843d8d80856c0a5
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

Loading…