Diisopropyl Ether → 3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid

HRID 499333Notes

Reaction equation

HRID 499333 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]=[C:16]([CH2:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:15]=[CH:14][CH: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[N:17]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 22939300tert-Butyl 3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate

Product 1

HCID 99013333-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acidYield 77%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate (0.50 g, 1.4 mmol) was dissolved in trifluoroacetic acid (3 ml) under ice cooling condition, and the mixture was stirred for 2.5 hrs. The reaction mixture was combined with isopropylether to give the precipitated solid, which was collected by filtration and recrystallized from tetrahydrofuran-ethanol to give the titled compound (0.33 g, 77%) as white crystals.

Workup

  1. customto give the precipitated solid, which
  2. filtrationwas collected by filtration
  3. customrecrystallized from tetrahydrofuran-ethanol

Sources & evidence

ORD record
ord-b5bddc0404e04f848ca8a5aaebecd128
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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