Trifluoroacetic acid → HCID 59750273, compound

HRID 748165Notes

Reaction equation

HRID 748165 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[CH:14][CH:13]=2)=[N:3]1.FC(F)(F)C(O)=O>>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:14][CH:13]=2)=[N:3]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86628980HCID 86628980, compound

Product 1

HCID 59750273HCID 59750273, compoundYield 66%

Procedure

tert-Butyl 3-{3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-3-pyridyl]propoxy}propanoate (1.0 g, 2.3 mmol) and trifluoroacetic acid (4.0 ml) was stirred under ice cooling condition for 5 hrs. The reaction mixture was concentrated under reduced pressure, diluted with chloroform, washed with water and dried. The solvent was evaporated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-methanol (20:1, v/v) and recrystallized from chloroform-ethyl acetate to give the titled compound (0.55 g, 66%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with chloroform
  3. washwashed with water
  4. customdried
  5. customThe solvent was evaporated
  6. washeluted with ethyl acetate-methanol (20:1
  7. customv/v) and recrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-7eaaffeed29e425d9b6cbf4aa6b318b3
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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