Trifluoroacetic acid → HCID 178503635, compound

HRID 723147Notes

Reaction equation

HRID 723147 reaction equation
C(OC(=O)[NH:7][C:8]([C:10]1[S:11][C:12]([S:61][CH3:62])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([NH:31][C:32]([NH:41]C(OC(C)(C)C)=O)=[N:33]C(OC(C)(C)C)=O)=[CH:26][C:25]=3[NH:49][C:50]([NH:52][CH2:53][CH2:54][CH2:55][CH2:56][S:57]([CH3:60])(=[O:59])=[O:58])=[O:51])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])(C)(C)C.[F:64][C:65]([F:70])([F:69])[C:66]([OH:68])=[O:67]>C(Cl)Cl>[F:64][C:65]([F:70])([F:69])[C:66]([OH:68])=[O:67].[NH:31]([C:27]1[CH:28]=[C:29]([CH3:30])[C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([C:13]3[CH:14]=[C:10]([C:8]([NH2:9])=[NH:7])[S:11][C:12]=3[S:61][CH3:62])(=[O:16])=[O:17])[CH:19]=2)=[C:25]([NH:49][C:50]([NH:52][CH2:53][CH2:54][CH2:55][CH2:56][S:57]([CH3:60])(=[O:59])=[O:58])=[O:51])[CH:26]=1)[C:32]([NH2:41])=[NH:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178503638HCID 178503638, compound

Product 1

HCID 178503635HCID 178503635, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with [(4-{4′-(N′,N″-di-tert-butoxycarbonyl-guanidino)-2′-[3-(4-methanesulfonyl-butyl)-ureido]-6′-methyl-biphenyl-3-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester (110 mg, 0.116 mmol) was added a solution of trifluoroacetic acid in DCM (3.0 mL, 50%) and stirred at ambient temperature for 1 h. The mixture was concentrated, and purified by HPLC (C18-column, 5–50% CH3CN in H2O over 15 min.) to give the title compound (63 mg, 62% yield) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by HPLC (C18-column, 5–50% CH3CN in H2O over 15 min.)

Sources & evidence

ORD record
ord-cbc677523d93404289243499563bad49
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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