Potassium Bicarbonate → HCID 71060086, compound

HRID 337231Notes

Reaction equation

HRID 337231 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:23]=[CH:22][C:15]([CH2:16]OS(C)(=O)=O)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)([CH3:27])([CH3:26])[CH3:25].C(=O)(O)[O-].[K+]>CN(C=O)C>[C:24]([O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][N:34]([CH2:16][C:15]2[CH:22]=[CH:23][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[CH:13][CH:14]=2)[CH2:33][CH2:32]1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 86674089HCID 86674089, compound

Product 1

HCID 71060086HCID 71060086, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methanesulfonic acid 4-benzyloxycarbonylamino-benzyl ester (0.35 g, 2.5 mmol) was added to a suspension of piperidin-4-yl-carbamic acid tert-butyl ester (0.15 g, 0.76 mmol) and potassium bicarbonate (0.35 g, 2.5 mmol) in DMF (10 ml) and the reaction heated to 60° C. and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time, the reaction mixture was cooled to room temperature and the solvent removed. The resulting residue was diluted with EtOAc (50 ml) and washed with water (10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated and the resulting residue was triturated with EtOAc, the resulting precipitate collected by filtration and dried under vacuum to give the title compound (0.14 g, 37% yield) as a white solid. Tr=1.58 min, m/z (ES+) (M+H)+ 440.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. customthe solvent removed
  3. additionThe resulting residue was diluted with EtOAc (50 ml)
  4. washwashed with water (10 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe resulting residue was triturated with EtOAc
  10. filtrationthe resulting precipitate collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-c31f89fb58414edc9a0103bc9feba2f3
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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