Trifluoroacetic acid → HCID 86674474, compound

HRID 75179Notes

Reaction equation

HRID 75179 reaction equation
C(=O)(OC(C)(C)C)[O:2][N:3]([CH2:9][CH2:10][C:11]([C:13]#[N:14])=[CH2:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CN(C)C=O>[C:13]([CH:11]1[CH2:12][O:2][N:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:9][CH2:10]1)#[N:14]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86674469(3-Cyano-3-butene-1-yl)(ethoxycarbonyl)azanyl 1,1-dimethylethyl carbonate2×

Product 1

HCID 86674474HCID 86674474, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (3-cyano-3-butene-1-yl)(ethoxycarbonyl)azanyl 1,1-dimethylethyl carbonate (i.e. the product of Step G) and trifluoroacetic acid (3 mL) in dichloromethane (40 mL) was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure to a tan oil. The oil was combined with potassium carbonate (3.6 g, 0.026 mol) in N,N-dimethylformamide (30 mL) and stirred at 80° C. for 24 h. The reaction mixture was concentrated under reduced pressure to near dryness. Methanol and dichloromethane were added and the precipitated solids were removed by filtration. The resulting solid was adsorbed onto Celite® (diatomaceous filter aid), and then purified by silica gel chromatography to provide the title compound as a pale-tan oil (0.645 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a tan oil
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionMethanol and dichloromethane were added
  4. customthe precipitated solids were removed by filtration
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-591eba868f394f4289e137f67b973e02
Source dataset
uspto-grants-2014_09
Patent number
US08835427B2

Reaction notes

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