Trifluoroacetic acid → 3-[6-(7-Methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid

HRID 499423Notes

Reaction equation

HRID 499423 reaction equation
[CH3:1][C:2]1[CH:27]=[CH:26][C:5]2[C:6](=[O:25])[N:7]=[C:8]([C:10]3[N:15]=[C:14]([CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH:13]=[CH:12][CH:11]=3)[S:9][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O>>[CH3:1][C:2]1[CH:27]=[CH:26][C:5]2[C:6](=[O:25])[N:7]=[C:8]([C:10]3[N:15]=[C:14]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:12][CH:11]=3)[S:9][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22939357HCID 22939357, compound

Product 1

HCID 597504403-[6-(7-Methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acidYield 101.1%

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl 3-[6-(7-methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate (0.40 g, 1.0 mmol) obtained in Example 175 and trifluoroacetic acid (5.0 ml) was stirred at 0° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure and combined with diisopropyl ether to precipitate crystals, which were collected by filtration and dried to give the titled compound (0.33 g, 97%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-d92b2029789a4ddc91f790bca3eba69f
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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