Acetic Acid → HCID 21839431, compound

HRID 1588396Notes

Reaction equation

HRID 1588396 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][CH:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][CH:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:19][C:20]1[CH:24]=[C:23]([CH3:25])[N-:22][N:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 62103,5-DimethylpyrazoleHCID 10868DicyclohexylcarbodiimideHCID 232388N-(Carbobenzyloxy)-DL-proline

Product 1

HCID 21839431HCID 21839431, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Benzyloxycarbonyl-DL-proline (4.98 g) was dissolved in dry dichloromethane (100 ml) and 3,5-dimethylpyrazole (2.12 g) and dicyclohexylcarbodiimide (4.5 g) were added to the solution at -20° C. After 30 min the temperature was elevated to room temperature and the solution was stirred for 20 h. After the completion of the reaction, 0.3 ml of acetic acid was added to the reaction mixture and an insoluble matter was removed by filtration. After the solvent was distilled off, the residue was dissolved in a small amount of ethyl acetate. An insoluble matter was removed by filtration and the filtrate was evaporated to dryness under reduced pressure to give 6.0 g of N-benzyloxycarbonyl-DL-proline-3,5-dimethylpyrazolide (yield: 91.7%).

Workup

  1. additionwas added to the reaction mixture
  2. customan insoluble matter was removed by filtration
  3. distillationAfter the solvent was distilled off
  4. dissolutionthe residue was dissolved in a small amount of ethyl acetate
  5. customAn insoluble matter was removed by filtration
  6. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a400a957f7af411fa72185769c64428b
Source dataset
uspto-grants-1993_06
Patent number
US05221752

Reaction notes

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