Trifluoroacetic acid → HCID 67001644, compound

HRID 1186233Notes

Reaction equation

HRID 1186233 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[N:5]2[CH2:13][CH2:14][N:15]([C:17]([O:19]C(C)(C)C)=O)[CH2:16][CH:4]2[CH2:3]1.FC(F)(F)C(O)=O.[F:31][C:32]1[CH:40]=[CH:39][C:35](C(Cl)=O)=[CH:34][CH:33]=1>C(Cl)Cl>[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:17]([N:15]2[CH2:14][CH2:13][N:5]3[C:6]4[N:12]=[CH:11][CH:10]=[CH:9][C:7]=4[NH:8][C:2](=[O:1])[CH2:3][CH:4]3[CH2:16]2)=[O:19])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 678794-Fluorobenzoyl chlorideHCID 67001482HCID 67001482, compound

Product 1

HCID 67001644HCID 67001644, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of the product of Example 64A (0.50 g, 1.570 mmol) in CH2Cl2 (3 mL) was stirred with ice cooling as trifluoroacetic acid (2 mL) was added over 1 minute. The resulting solution was stirred at 0° C. for 50 minutes and then allowed to warm to room temperature for 1 hour. The mixture was concentrated under vacuum, and the residue was taken up in 6% NaOH (12 mL) and CH2Cl2 (5 mL), and p-fluorobenzoyl chloride (0.45 g, 2.8 mmol) was added. The mixture was stirred at room temperature for 13 hours and then filtered through diatomaceous earth with a CHCl3 (25 mL) rinse. The aqueous layer was extracted with CHCl3 (2×25 mL) and the combined extract was dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography (SiO2, CH2Cl2-methanol-15 M NH4OH, 95:5:0.5) to provide the title compound: MS (DCI) m/z 341 (M+H)+.

Workup

  1. additionwas added over 1 minute
  2. temperatureto warm to room temperature for 1 hour
  3. concentrationThe mixture was concentrated under vacuum
  4. stirringThe mixture was stirred at room temperature for 13 hours
  5. filtrationfiltered through diatomaceous earth with a CHCl3 (25 mL)
  6. washrinse
  7. extractionThe aqueous layer was extracted with CHCl3 (2×25 mL)
  8. extractionthe combined extract
  9. dry with materialwas dried (Na2SO4)
  10. concentrationconcentrated under vacuum
  11. customThe residue was purified by chromatography (SiO2, CH2Cl2-methanol-15 M NH4OH, 95:5:0.5)

Sources & evidence

ORD record
ord-614caad7cdf54201977c2e61f1836470
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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