Chloroform trifluoroacetic acid → N-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-4-trifluoromethanesulfonylamino-butyramide trifluoroacetate

HRID 723181Notes

Reaction equation

C(Cl)(Cl)Cl.[F:5][C:6]([F:11])([F:10])[C:7]([OH:9])=[O:8].C(OC(=O)[NH:18][C:19](=[NH:57])[C:20]1[S:21][C:22]([S:55][CH3:56])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[NH:41][C:42](=[O:54])[CH2:43][CH2:44][CH2:45][NH:46][S:47]([C:50]([F:53])([F:52])[F:51])(=[O:49])=[O:48])[CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:24]=1)(C)(C)C>>[F:5][C:6]([F:11])([F:10])[C:7]([OH:9])=[O:8].[C:19]([C:20]1[S:21][C:22]([S:55][CH3:56])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[NH:41][C:42](=[O:54])[CH2:43][CH2:44][CH2:45][NH:46][S:47]([C:50]([F:52])([F:53])[F:51])(=[O:48])=[O:49])[CH:31]=[CH:32][CH:33]=2)(=[O:26])=[O:27])[CH:24]=1)(=[NH:18])[NH2:57]

Participants

Reactant 2

HCID 19978452Chloroform trifluoroacetic acid

HCID 145857667CID 145857667

Product 1

HCID 21886372N-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-4-trifluoromethanesulfonylamino-butyramide trifluoroacetateYield 54%

Procedure

A solution of dichloromethane/trifluoroacetic acid (1/1) [2 mL] was added to (imino-{5-methylsulfanyl-4-[6′-methyl-2′-(4-trifluoromethanesulfonylaminobutyrylamino)-biphenyl-3-sulfonyl]-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester (0.020 g, 0.027 mmol) [example 212, step c] at room temperature and stirred for 1 hour. The reaction mixture was evaporated and purified via reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to give the title compound (0.009 g, 54%) as a solid. 1H-NMR (MeOD): δ 8.29 (s, 1H), 8.03 (md, 1H, J=8.4 Hz), 7.87 (m, 1H), 7.68 (t, 1H, J=7.6 Hz), 7.53 (md, 1H, J=7.6 Hz), 7.34 (t, 1H, J=7.6 Hz), 7.28 (d, 1H, J=7.2 Hz), 7.19 (d, 1H, J=7.2 Hz), 2.98 (m, 2H), 2.72 (s, 3H), 2.06 (s, 3H), 2.05 (t, 2H, J=7.6 Hz), 1.48 (m, 2H). ESI-MS (m/z): Calcd. for C24H25F3N4O5S4: 634.07; found: 635.1.

Workup

customThe reaction mixture was evaporated
custompurified via reverse-phase HPLC [acetonitrile/water (0.01% TFA)]

Sources & evidence

ORD record: ord-347256a126a345f193fb3dfaa920a3f5
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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