Trifluoroacetic acid → 2-((2,3-Dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoic acid

HRID 2191710Notes

Reaction equation

HRID 2191710 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:13]2[CH:14]=[CH:15][C:16]([NH:18][C:19]3[CH:31]=[C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:29]=[CH:28][C:20]=3[C:21]([O:23]C(C)(C)C)=[O:22])=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1>>[O:8]1[C:13]2[CH:14]=[CH:15][C:16]([NH:18][C:19]3[CH:31]=[C:30]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:29]=[CH:28][C:20]=3[C:21]([OH:23])=[O:22])=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68959355Tert-butyl 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoate

Product 1

HCID 576679712-((2,3-Dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoic acid

Procedure

Trifluoroacetic acid 3.0 mL solution of the obtained tert-butyl 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoate 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; 70-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoic acid 5 mg of a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d6c628cd439b47f49ba6e62692897af0
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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