Trifluoroacetic acid → HCID 178522352, compound

HRID 469708Notes

Reaction equation

C[O:2][C:3]1(OC)[C:9]([NH:10][C:11]([C:13]2[C:14]([OH:23])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:12])=[CH:8][C:7](=[O:24])[CH:6]2[CH:4]1[O:5]2.FC(F)(F)C(O)=O>>[O:2]=[C:3]1[C:9]([NH:10][C:11]([C:13]2[C:14]([OH:23])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:12])=[CH:8][C:7](=[O:24])[CH:6]2[CH:4]1[O:5]2

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178494373HCID 178494373, compound

Product 1

HCID 178522352HCID 178522352, compoundYield 102.1%

Procedure

To a flask containing N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxyquinoline-3-carboxamide (65 mg, 0.18 mmol) was added trifluoroacetic acid (15 mL) in one portion. The solution was stirred 3 hours, after which the reaction was judged complete by LC-MS. The trifluoroacetic acid was removed in vacuo and the product dried with a stream of nitrogen to afford 57 mg (100%) of the title product that contained ca. 15% of a byproduct that was suggested to be the hydrolyzed product (at both amide and epoxide positions; M+ 204). The solid was used in the next step without additional characterization or purification.

Workup

customThe trifluoroacetic acid was removed in vacuo
customthe product dried with a stream of nitrogen

Sources & evidence

ORD record: ord-7f7b2c65426d46a79f89eb65e512f0e0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629164B2

Reaction notes

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