Trifluoroacetic acid → HCID 178434759, compound

HRID 1633735Notes

Reaction equation

HRID 1633735 reaction equation
[CH3:1][C:2]1[C:6]([S:7]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][CH2:15][CH:16]3[C:21]2[N:22]=[CH:23][N:24](C(OC(C)(C)C)=O)[CH:25]=2)(=[O:9])=[O:8])=[C:5]([CH3:33])[O:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[NH:24]1[CH:25]=[C:21]([CH:16]2[CH2:15][CH2:14][CH2:13][C:12]3[C:11]([NH:10][S:7]([C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:33])(=[O:9])=[O:8])=[CH:20][CH:19]=[CH:18][C:17]2=3)[N:22]=[CH:23]1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18679769HCID 18679769, compound

Product 1

HCID 178434759HCID 178434759, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A 0° C. solution of Example 61A (150 mg, 0.318 mmol) in methylene chloride (10 mL) was treated with trifluoroacetic acid (3.2 mL) and stirred for 1.5 hours. The reaction mixture was warmed to room temperature for 2 hours and then cooled to −20° C. for 16 hours. The reaction mixture was warmed to ambient temperature and diluted with methylene chloride and water and neutralized with aqueous saturated NaHCO3. The methylene chloride layer was separated and the aqueous phase extracted twice more with methylene chloride. The combined extracts were dried (MgSO4), filtered, and concentrated under vacuum. The residue was chromatographed on flash silica gel (79:20:1 methylene chloride/methanol/ammonium hydroxide) to provide the title compound (87 mg, 0.23 mmol, 74% yield).

Workup

  1. temperaturecooled to −20° C. for 16 hours
  2. temperatureThe reaction mixture was warmed to ambient temperature
  3. customThe methylene chloride layer was separated
  4. extractionthe aqueous phase extracted twice more with methylene chloride
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was chromatographed on flash silica gel (79:20:1 methylene chloride/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-9e23aea3e5bf4f28b73973e6f6c3a390
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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