Triethylamine → 1-(N,N'-Bis(tert-butoxycarbonyl)carbamimidoyl)piperidine-4-carboxylic acid

HRID 1053814Notes

Reaction equation

HRID 1053814 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1.C(N(CC)CC)C.[CH3:24][C:25]([O:28][C:29]([NH:31][C:32](N1C=CC=N1)=[N:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])([CH3:27])[CH3:26]>CO>[CH3:27][C:25]([O:28][C:29]([NH:31][C:32]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[N:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])([CH3:24])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 90014521Piperidine-4-carboxylic acid trifluoroacetate salt

Product 1

HCID 1317362991-(N,N'-Bis(tert-butoxycarbonyl)carbamimidoyl)piperidine-4-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of piperidine-4-carboxylic acid trifluoroacetate salt (0.20 g, 0.82 mmol) in methanol (10 mL), triethylamine (0.20 mL, 1.6 mmol) and N,N′-bis{[(2-methyl-2-propanyl)oxy]carbonyl}-1H-pyrazole-1-carboximidamide (0.30 g, 0.98 mmol) was added and the reaction mixture stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure and the resulting residue dissolved in ethyl acetate and washed with brine. The organic layer was dried and concentrated to dryness to obtain the title compound (200 mg, 76%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe resulting residue dissolved in ethyl acetate
  3. washwashed with brine
  4. customThe organic layer was dried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-83991b3e84934ade90b87135aac581d9
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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