Trifluoroacetic acid → HCID 59750345, compound

HRID 499641Notes

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][O:19][CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[CH:15]=[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]=[C:16]([CH2:18][O:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59750339HCID 59750339, compound

Product 1

HCID 59750345HCID 59750345, compoundYield 76.5%

Conditions

Temperature: 0 °C

Procedure

A mixture of tert-butyl 3-[(6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl)methoxy]propanoate (2.80 g, 6.8 mmol) and trifluoroacetic acid (15 ml) was stirred at 0° C. for 3 hrs. The mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate-hexane to give the titled compound (1.78 g, 74%), which was recrystallized from ethanol to give prisms (1.66 g, 69%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-bde2864c47a94c7790a2bf63145579e6
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767665B2

Reaction notes

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