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

HRID 358304Notes

Reaction equation

HRID 358304 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.[Cl:23][C:24]([Cl:28])([Cl:27])[CH2:25]O.N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:23][C:24]([Cl:28])([Cl:27])[CH2:25][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

6

Reactant 4

HCID 1049PyridineHCID 8259TrichloroethanolHCID 10868DicyclohexylcarbodiimideHCID 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 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran were dissolved 1.53 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine and 1 ml of 2,2,2-trichloroethanol and under cooling at 0°-5° C., 0.8 ml of pyridine was added. Then, 1.2 g of dicyclohexylcarbodiimide was added and the mixture was stirred at the same temperature as above for 2 hours and at room temperature for 18 hours. The precipitated dicyclohexylurea separating out was filtered off and the filtrate was concentrated under reduced pressure. The residue was added to a mixture of 2 N hydrochloric acid and ethyl acetates and 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 crystallized from ethyl ether-petroleum ether. Yield 0.7 g.

Workup

  1. temperatureunder cooling at 0°-5° C.
  2. filtrationThe precipitated dicyclohexylurea separating out was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was added to a mixture of 2 N hydrochloric acid and ethyl acetates
  5. customthe ethyl acetate layer was separated
  6. washwashed with 2 N hydrochloric acid
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was chromatographed on a silica gel column
  10. washeluted with toluene-ethyl acetate (3:1)
  11. concentrationThe eluate was concentrated under reduced pressure
  12. customthe residue was crystallized from ethyl ether-petroleum ether

Sources & evidence

ORD record
ord-db8cfefebcd747d9bcccd17ef916849c
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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