Trifluoroacetic acid → HCID 69298540, compound

HRID 2054607Notes

Reaction equation

HRID 2054607 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:51]=[CH:50][C:24]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([N:34]4[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH:36]([C:47]([O-:49])=[O:48])[CH2:35]4)(=[O:33])=[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]([S:31]([N:34]4[CH2:39][CH2:38][NH:37][CH:36]([C:47]([OH:49])=[O:48])[CH2:35]4)(=[O:33])=[O:32])=[CH:29][CH:30]=3)=[CH:50][CH:51]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726766HCID 131726766, compound

Product 1

HCID 69298540HCID 69298540, compoundYield 100.4%

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-sulfonyl)-piperazine-1,2-dicarboxylic acid, 1-tert-butyl ester (120 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 (101 mg, 100%): Rf 0.10 (20% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz): δ 8.19 (2H, t, J=9 Hz, Ar—H), 8.08 (4H, m Ar—H), 7.94 (4H, m, Ar—H), 7.74 (2H, t, J=9, 4 Hz, Ar—H), 7.54 (2H, m, Ar—H), 7.44 (1H, t, J=8 Hz, Ar—H), 4.38 (1H, m, CHN), 3.71 (1H, m), 3.46 (2H, m), 3.19 (1H, m), 2.98 (1H, m), 2.83 (1H, m), 1.41 (9H, s, CMe3); ESI-LCMS e/z calcd for C29H24N2O5S 612.700, found 635 (M+Na)+.

Workup

  1. concentrationconcentrated from methanol (3×10 mL)

Sources & evidence

ORD record
ord-5e544b21c1b24780a3e8a63d867f8cf3
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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