Trifluoroacetic acid → HCID 9817342, compound

HRID 1594234Notes

Reaction equation

HRID 1594234 reaction equation
C(OC(=O)[NH:7][C:8]1[S:12][C:11]2[CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:15]=[CH:16][C:10]=2[C:9]=1[C:24](=[O:26])[NH2:25])(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:8]1[S:12][C:11]2[CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH:15]=[CH:16][C:10]=2[C:9]=1[C:24]([NH2:25])=[O:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69679484HCID 69679484, compound

Product 1

HCID 9817342HCID 9817342, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1h (20 mg, 0.051 mmol) in CH2Cl2 (5 mL) was mixed with trifluoroacetic acid (0.5 mL). The resultant solution was stirred at room temperature for 1 h, then mixed with saturated NaHCO3 solution (30 mL), and extracted with ethyl acetate (30 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 1:1) provided the title compound (8 mg, 55%) as a white solid: MS (ES) m/z 287 (M+H)+; 1H NMR (400 MHz, CD3OD) δ7.73 (s, 1H), 7.63-7.50 (m, 3H), 7.42 (m, 1H), 7.08 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (30 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-970fdd89fc45421d990fc46b135e39a9
Source dataset
uspto-grants-2007_11
Patent number
US07300952B2

Reaction notes

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