Trifluoroacetic acid methylene chloride → HCID 21886275, compound

HRID 723136Notes

Reaction equation

HRID 723136 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:40])[C:9]1[S:10][C:11]([S:38][CH3:39])=[C:12]([S:14]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])=[CH:25][C:24]=3[CH3:37])[CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].C(Cl)Cl>>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[CH3:39][S:38][C:11]1[S:10][C:9]([C:8]([NH2:40])=[NH:7])=[CH:13][C:12]=1[S:14]([C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([C:33]([F:35])([F:34])[F:36])(=[O:31])=[O:32])=[CH:25][C:24]=2[CH3:37])[CH:20]=[CH:21][CH:22]=1)(=[O:15])=[O:16]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 145857689HCID 145857689, compound

Product 1

HCID 21886275HCID 21886275, compoundYield 54%

Procedure

A mixture of {imino-[5-methylsulfanyl-4-(2′-methyl-4′-trifluoromethanesulfonylamino-biphenyl-3-sulfonyl)-thiophen-2-yl]-methyl}-carbamic acid tert-butyl ester (9 mg, 14 μmol) in TFA/DCM (1:1, 3 mL) was stirred at ambient temperature for 40 min. The mixture was concentrated, and flashed chromatographed on silica gel column, eluting with MeOH/DCM (5 to 8%) to give the title compound (5 mg, 54% yield) as a pale yellow solid. 1H NMR (CDCl3): δ 8.32 (s, 1H), 8.04–8.01 (m, 1H), 7.96–7.95 (m, 1H), 7.68–7.66 (m, 2H), 7.17 (m, 3H), 2.72 (s, 3H), 2.21 (s, 3H), ESI-MS (m/z): Cald. For C20H19F3N3O4S4: 550.0 (M+H); found: 550.0.

Workup

  1. concentrationThe mixture was concentrated
  2. customflashed chromatographed on silica gel column
  3. washeluting with MeOH/DCM (5 to 8%)

Sources & evidence

ORD record
ord-8cfcc209375d4ecc9632f16800df6836
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…