Diisopropyl Ether → 3-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propionic acid

HRID 748408Notes

Reaction equation

HRID 748408 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[CH:17]=[C:16]([CH2:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:15]=[CH:14][N:13]=2)=[N:3]1.C(OC(C)C)(C)C>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[CH:17]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:14][N:13]=2)=[N:3]1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 22939427HCID 22939427, compound

Product 1

HCID 597503013-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propionic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-[2-(4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propionate (0.45 g, 1.2 mmol) was dissolved in trifluoroacetic acid (3.0 ml), and the mixture was stirred at room temperature for 2.5 hrs. Isopropyl ether was added to the reaction mixture to precipitate crystals, which were collected by filtration and washed with ethanol-hexane to give the titled compound (0.32 g, 84%) as white crystals.

Workup

  1. customto precipitate crystals, which
  2. filtrationwere collected by filtration
  3. washwashed with ethanol-hexane

Sources & evidence

ORD record
ord-7a8939e6155c4ac4ae4a78d04cd30b33
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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