Diazomethane → Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester

HRID 358299Notes

Reaction equation

HRID 358299 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.[N+](=[CH2:25])=[N-]>CO>[CH3:25][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

4

Reactant 2

HCID 9550DiazomethaneHCID 13105388Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

Product 1

HCID 13105389Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 300 ml of methanol was dissolved 2 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine and under ice-cooling an excess of an ethereal solution of diazomethane was added. The mixture was stirred under ice-cooling for 2 hours and then concentrated 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 after addition of ethyl ether to the residue, the mixture was allowed to stand in a refrigerator overnight to give crystals. Yield 1.3 g.

Workup

  1. additionwas added
  2. temperaturecooling for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was chromatographed on a silica gel column
  5. washeluted with toluene-acetone (4:1)
  6. concentrationThe eluate was concentrated under reduced pressure
  7. additionafter addition of ethyl ether to the residue
  8. customto stand in a refrigerator overnight
  9. customto give crystals

Sources & evidence

ORD record
ord-fd959fd963ff44a7953b5ff8514ef000
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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