Dimethylformamide → HCID 14672925, compound

HRID 1639264Notes

Reaction equation

HRID 1639264 reaction equation
ClC([O:4][CH2:5][CH:6]([CH3:8])C)=O.[CH2:9]([N:11]([CH2:14]C)CC)C.[CH3:16]Cl.NC[C:20]([OH:22])=[O:21].[CH3:23][N:24](C)[CH:25]=[O:26]>>[CH3:16][O:22][C:20](=[O:21])[CH2:23][NH:24][C:25](=[O:26])[CH2:9][N:11]1[CH2:14][CH2:8][CH2:6][C:5]1=[O:4]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 86743526HCID 86743526, compound

Product 1

HCID 14672925HCID 14672925, compound

Procedure

18.5 g of 2-oxo-1 pyrrolidinyl acetic acid was dissolved in 500 ml of dimethylformamide and the solution was cooled to -15° C., to which 18.53 g of isobutyl chloroformate was added and 13.21 g of triethylamine was added dropwise at -15° to 5° C. After stirring at -10° to -5° C. for 15 minutes, 17.04 g of glycine methyl hydrochloride was added and 13.73 g of triethylamine was added dropwise at -10° to -5° C. The reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours and triethylamine hydrochloride was filtered off. Dimethylformamide was distilled off under reduced pressure and the residue was purified through the chromatography on silica gel (silica gel 500 g, chloroform-1 to 2 % of methanol as the eluent). Then, the solvent was distilled off to obtain 17.97 g of N- [ (2-oxo-1-pyrrolidinyl)acetyl]glycine methyl ester as the oily substance. This was dissolved in 100 ml of methanol and the solution of 4.78 g of sodium hydroxide dissolved in 150 ml of methanol was added thereto and reacted at room temperature for 12 hours. After 10 g of acetic acid was added, methanol was distilled off under reduced pressure and the residue was purified through the chromatography on silica gel (silica gel 340 g, chloroform-10 % of methanol-1 % of formic acid as the eluent). The solvent was distilled off and the residue was crystallized from tetrahydrofuran to obtain the titled compound.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. customto room temperature
  4. customover 2 hours
  5. filtrationtriethylamine hydrochloride was filtered off
  6. distillationDimethylformamide was distilled off under reduced pressure
  7. customthe residue was purified through the chromatography on silica gel (silica gel 500 g, chloroform-1 to 2 % of methanol as the eluent)
  8. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-9c27623e16374e2faf6b712c7b306532
Source dataset
uspto-grants-1989_11
Patent number
US04883802

Reaction notes

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