Trifluoroacetic acid → HCID 59655961, compound

HRID 2054606Notes

Reaction equation

HRID 2054606 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:50]=[CH:49][C:24]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([N:33]4[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH:35]([C:46]([O-:48])=[O:47])[CH2:34]4)=[O:32])=[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]([C:31]([N:33]4[CH2:38][CH2:37][NH:36][CH:35]([C:46]([OH:48])=[O:47])[CH2:34]4)=[O:32])=[CH:29][CH:30]=3)=[CH:49][CH:50]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726764HCID 131726764, compound

Product 1

HCID 59655961HCID 59655961, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of 4-(4′-Dibenzofuran-4-ylbiphen-4-yl-carbonyl)-piperazine-1,2-dicarboxylic acid, 1-tert-butyl ester (135 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 (112 mg, 100%): Rf 0.10 (20% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz): δ 8.18 (2H, t, J=9 Hz, Ar—H), 8.04 (2H, d, J=9 Hz, Ar—H), 7.92 (2H, d, J=9 Hz, Ar—H), 7.86 (2H, d, J=9 Hz, Ar—H), 7.75 (2H, t, J=8 Hz, Ar—H), 7.61 (2H, m, Ar—H), 7.53 (2H, t, q, J=8 Hz, Ar—H), 7.43 (1H, t, J=8 Hz, Ar—H), 4.34 (1H, m, CHN), 3.40 (4H, m), 3.18 (2H, m); ESI-LCMS e/z calcd for C30H24N2O4 476.530, found 477 (M+H)+, 499 (M+Na)+.

Workup

  1. concentrationconcentrated from methanol (3×10 mL)

Sources & evidence

ORD record
ord-01dfb1b0c3f44a318b13702e86174829
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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