Acetic Acid → HCID 54160971, compound

HRID 361379Notes

Reaction equation

HRID 361379 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([CH3:15])=[C:13]([C:16]#[N:17])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>CO.[Pd]>[NH2:17][CH2:16][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:14]=1[CH3:15]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 53973781HCID 53973781, compound

Product 1

HCID 54160971HCID 54160971, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 175 mg (0.75 mmol) of 2-t-butyloxycarbonylamino-4-cyano-3-methylpyridine and 88 μL (1.5 mmol) of acetic acid in 10 mL of MeOH was hydrogenated over 75 mg of 10% Pd-C at 55 psi overnight on a Parr apparatus. The catalyst was removed by filtration, concentrated at reduced pressure, and the residue partitioned between CHCl3 and 10% Na2CO3. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried over Na2SO4 and concentrated to give 150 mg of the title compound as a colorless oil:

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationconcentrated at reduced pressure
  3. customthe residue partitioned between CHCl3 and 10% Na2CO3
  4. extractionThe aqueous layer was extracted with CHCl3
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0051d14455844d1b6c3977e9a7e5d13
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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