3,5-Dimethylpyrazole → HCID 22811195, compound

HRID 1706012Notes

Reaction equation

HRID 1706012 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]1[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:27][C:28]1[CH:32]=[C:31]([CH3:33])[N-:30][N:29]=1

Participants

5

Reactant 3

HCID 62103,5-DimethylpyrazoleHCID 10868DicyclohexylcarbodiimideHCID 22811196HCID 22811196, compound

Product 1

HCID 22811195HCID 22811195, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Benzyloxycarbonyl-4-benzyloxy-L-proline (4.55 g.) [obtained from 4-benzyloxyproline [Biochem. Biophys. Acta 303, 198 (1973)] and benzyloxycarbonyl chloride] and 3,5-dimethylpyrazole (1.15 g.) are dissolved in chloroform (200 ml.). Dicyclohexylcarbodiimide (2.06 g.) is added and the mixture is stirred in an ice-salt bath for one hour and at room temperature for 16 hours. The precipitate is filtered and the filtrate is concentrated to dryness. The residue is dissolved in ethyl acetate, washed with N-hydrochloric acid and water. The organic layer is dried and concentrated to dryness in vacuo to yield 1-benzyloxycarbonyl-4-benzyloxy-L-proline-3,5-dimethylpyrazolide.

Workup

  1. filtrationThe precipitate is filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with N-hydrochloric acid and water
  5. customThe organic layer is dried
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-44925fa62561460ba341f6d811179974
Source dataset
uspto-grants-1980_06
Patent number
US04206122

Reaction notes

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