tert-Butyl 6-[[4-oxo-2-(2-pyridyl)-4H-1,3-benzothiazin-6-yl]oxy]hexanoate → 6-[[4-Oxo-2-(2-pyridyl)-4H-1,3-benzothiazin-6-yl]oxy]hexanoic acid

HRID 748186Notes

Reaction equation

HRID 748186 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:3]1>FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:3]1

Participants

3

Reactant 1

HCID 68459181tert-Butyl 6-[[4-oxo-2-(2-pyridyl)-4H-1,3-benzothiazin-6-yl]oxy]hexanoate

Product 1

HCID 576253396-[[4-Oxo-2-(2-pyridyl)-4H-1,3-benzothiazin-6-yl]oxy]hexanoic acidYield 103.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl 6-[[4-oxo-2-(2-pyridyl)-4H-1,3-benzothiazin-6-yl]oxy]hexanoate (0.80 g, 1.8 mmol) and trifluoroacetic acid (10 ml) was stirred under ice cooling condition for 1 hr. The reaction mixture was concentrated under reduced pressure and crystallized from diisopropyl ether to give the titled compound (0.69 g, ca. 100%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2e8bf5339fd8475aa209f67a560b82b5
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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