Trifluoroacetic acid → HCID 59655970, compound

HRID 2054605Notes

Reaction equation

HRID 2054605 reaction equation
FC(F)(F)C(O)=O.[CH:8]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[C:11]([C:21]2[CH:49]=[CH:48][C:24]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][N:32]4[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH:34]([C:45]([O-:47])=[O:46])[CH2:33]4)=[CH:27][CH:26]=3)=[CH:23][CH:22]=2)=[CH:10][CH:9]=1>ClCCl>[CH:8]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[C:11]([C:21]2[CH:22]=[CH:23][C:24]([C:25]3[CH:26]=[CH:27][C:28]([CH2:31][N:32]4[CH2:37][CH2:36][NH:35][CH:34]([C:45]([OH:47])=[O:46])[CH2:33]4)=[CH:29][CH:30]=3)=[CH:48][CH:49]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726763HCID 131726763, compound

Product 1

HCID 59655970HCID 59655970, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of 4-(4′-Dibenzofuran-4-ylbiphen-4-ylmethyl)-piperazine-1,2-dicarboxylic acid, 1-tert-butyl ester (80 mg) in anhydrous dichloromethane. The reaction was stirred at room temperature for 2 hours (TLC control). The resultant brown oil was reconstituted and concentrated from methanol (3×10 mL) and then from dichloromethane (2×10 mL) to give the title compound as a white solid (65 mg, 100%): Rf 0.25 (20% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz): δ 8.19 (1H, d, J=9 Hz, Ar—H), 8.16 (1H, d, J=9 Hz, Ar—H), 8.01 (2H, d, J=9 Hz, Ar—H), 7.86 (2H, d, J=9 Hz, Ar—H), 7.72 (4H, m, Ar—H), 7.53 (2H, q, J=8 Hz, Ar—H), 7.45 (3H, m, Ar—H), 4.22 (1H, m, CHN), 3.78 (2H, s), 3.35 (1H, m), 3.08 (2H, m), 2.86 (1H, m), 2.58 (2H, m); ESI-LCMS e/z calcd for C30H26N2O3 462.546, found 563 (M+H)+.

Workup

  1. concentrationconcentrated from methanol (3×10 mL)

Sources & evidence

ORD record
ord-1a454e444d7f4ad38afa3e4d9a71f61c
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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