Acetonitrile → HCID 23565296, compound

HRID 1920141Notes

Reaction equation

HRID 1920141 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](#N)[CH3:16].CC[C:20]([C:22](Cl)=[O:23])=[O:21].C(=O)([O-])[OH:26].[Na+]>C(N(CC)CC)C>[CH2:15]([O:26][C:20](=[O:21])[C:22]([N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][CH2:13]1)=[O:23])[CH3:16]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 11007880Butanoyl chloride, 2-oxo-

Product 1

HCID 23565296HCID 23565296, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-(tert-butoxycarbonylamino)piperidine (150 mg) was added to acetonitrile (5 mL), and triethylamine (0.21 mL) and ethyloxalyl chloride (0.11 mL) were added dropwise at 0° C. The reaction solution was stirred for 30 minutes and an aqueous saturated sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound (235 mg) having the following physical properties.

Workup

  1. additionwere added dropwise at 0° C
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed in turn with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2263cba02e1a44da97043bf920c71c42
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

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