Acetonitrile → HCID 67777124, compound

HRID 1026274Notes

Reaction equation

HRID 1026274 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:21])[CH2:10][O:11][C:12]1[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[NH:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.C(#N)C>O>[Br:22][C:16]1[C:12]([O:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:21])=[N:13][NH:14][C:15]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 67778799HCID 67778799, compound

Product 1

HCID 67777124HCID 67777124, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-1H-pyrazole-5-carboxylate (2.00 g), N-bromosuccinimide (1.43 g) and acetonitrile (50 mL) was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white powder (2.20 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-62dc2ce80bd14155963f99831a125931
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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