Acetic Acid → HCID 21839431, compound

HRID 1292537Notes

Reaction equation

HRID 1292537 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

After 4.98 g of N-benzyloxycarbonyl-D,L-proline was dissolved in 100 ml of dichloromethane, 2.12 g of 3,5-dimethylpyrazole and 4.5 g of dicyclohexylcarbodiimide were added to the solution. The temperature was reverted to room temperature 30 minutes after the addition and stirring was continued for 20 hours. At the end of the reaction, 0.3 ml of acetic acid was added to the reaction mixture. Insoluble matters were filtered off and the solvent was removed by distillation. The residue was dissolved in a small volume of ethyl acetate. After insoluble matters were filtered off, the filtrate was evaporated to dryness under vacuum to give 6.0 g (yield, 91.7%) of N-benzyloxycarbonyl-D,L-proline-3,5-dimethylpyrazolide.

Workup

  1. additionafter the addition
  2. waitwas continued for 20 hours
  3. additionwas added to the reaction mixture
  4. filtrationInsoluble matters were filtered off
  5. customthe solvent was removed by distillation
  6. dissolutionThe residue was dissolved in a small volume of ethyl acetate
  7. filtrationAfter insoluble matters were filtered off
  8. customthe filtrate was evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-4a084d4d823048089bca855e0818f6d5
Source dataset
uspto-grants-1998_05
Patent number
US05756763

Reaction notes

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