Trifluoroacetic acid → HCID 59751438, compound

HRID 748931Notes

Reaction equation

HRID 748931 reaction equation
[C:1]([N:5](C)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=3)[C:16]=2[O:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:30][CH:29]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[CH3:26][O:25][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[C:16]([O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:30][CH:29]=1)=[C:15]([C:12]1[CH:11]=[CH:10][C:9]([S:6]([NH:5][CH3:1])(=[O:8])=[O:7])=[CH:14][CH:13]=1)[CH:24]=[CH:23]2

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68518335HCID 68518335, compound

Product 1

HCID 59751438HCID 59751438, compoundYield 89%

Procedure

In a round bottom flask place the product of Example 68 (80 mg, 0.13 mmol) and trifluoroacetic acid (5 mL). Heat this solution at reflux for 15-20 minutes then cool to ambient temperature. Quench the reaction mixture by pouring it over saturated aqueous sodium bicarbonate then extract into ethyl acetate. Wash the combined extracts with saturated aqueous sodium bicarbonate, water and brine; then dry (sodium sulfate) and evaporate in vacuo. Purify the resulting material on a Chromatotron (silica gel; 4%-8% MeOH gradient in CH2Cl2) to obtain 63 mg of the title compound (89%). MS (IS+) m/e 547 (M+1).

Workup

  1. temperatureHeat this solution
  2. temperatureat reflux for 15-20 minutes
  3. customQuench the reaction mixture
  4. additionby pouring it over saturated aqueous sodium bicarbonate
  5. extractionthen extract into ethyl acetate
  6. washWash the combined extracts with saturated aqueous sodium bicarbonate, water and brine
  7. dry with materialthen dry (sodium sulfate)
  8. customevaporate in vacuo
  9. customPurify the resulting material on a Chromatotron (silica gel; 4%-8% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-e30d68a75be841baa3aafb449729f519
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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