Trifluoroacetic acid → HCID 68957208, compound

HRID 2191718Notes

Reaction equation

FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[CH:37]=[C:36]([CH2:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:35]=[CH:34][C:26]=3[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=O)(C)(C)C>>[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[CH:37]=[C:36]([CH2:38][CH2:39][C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:35]=[CH:34][C:26]=3[C:27]([OH:29])=[O:28])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68962177HCID 68962177, compound

Product 1

HCID 68957208HCID 68957208, compound

Procedure

Trifluoroacetic acid 3.0 mL solution of the obtained tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenethylbenzoate was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((1H-indol-5-yl)amino)-4-phenethylbenzoic acid 25 mg of pale yellow solid.

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-2c21005f0aeb4b6bbfd5519575d88519
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08327467B2

Reaction notes

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