Trifluoroacetic acid → HCID 57667802, compound

HRID 2191820Notes

Reaction equation

FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][C:18]3[CH:30]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([O:37]C(OC(C)(C)C)=O)[CH:32]=4)[CH:28]=[CH:27][C:19]=3[C:20]([O:22]C(C)(C)C)=[O:21])=[CH:16][C:11]=2[O:10][CH2:9]1>>[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][C:18]3[CH:30]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=4)[CH:28]=[CH:27][C:19]=3[C:20]([OH:22])=[O:21])=[CH:16][C:11]=2[O:10][CH2:9]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68962162HCID 68962162, compound

Product 1

HCID 57667802HCID 57667802, compound

Procedure

Trifluoroacetic acid 5.0 mL was added to the obtained tert-butyl 2-((benzo-1,3-dioxol-5-yl)amino)-4-(3-(tert-butoxycarbonyloxy)phenyl)benzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 50-90% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((benzo-1,3-dioxol-5-yl)amino)-4-(3-hydroxyphenyl)benzoic acid 17 mg of a yellow solid.

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-aa235568293d4755a34c998f7d458c68
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08327467B2

Reaction notes

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