Trifluoroacetic acid → 4-[2'-(1-Hydroxy-ethyl)-biphenyl-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

HRID 2216016Notes

Reaction equation

HRID 2216016 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:33])[C:9]1[S:10][C:11]([S:31][CH3:32])=[C:12]([S:14]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3C=C)[CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[OH:38][CH:37]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([S:14]([C:12]2[CH:13]=[C:9]([C:8]([NH2:7])=[NH:33])[S:10][C:11]=2[S:31][CH3:32])(=[O:15])=[O:16])[CH:18]=1)[CH3:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 145857708tert-butyl N-[4-[3-(2-ethenylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 218863604-[2'-(1-Hydroxy-ethyl)-biphenyl-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetateYield 33%

Procedure

{Imino-[5-methylsulfanyl-4-(2′-vinyl-biphenyl-3-sulfonyl)-thiophen-2-yl]-methyl}-carbamic acid tert-butyl ester (25 mg, 0.05 mmol) was treated with trifluoroacetic acid (50% in DCM) for 1 hr at rt. The reaction mixture was concentrated in vacuo and then basified with 1 M NaOH to pH 8 and allowed to stand for 10 min. The solution was then re-acidified with TFA and purified using C18-HPLC (10–80% CH3CN in H2O (0.1% TFA) over 30 min) to give 7 mg (33%) of the title compound as a white solid (Rt: 12.3 min). 1H-NMR (CD3OD): δ 8.32 (s, 1H), 8.01–8.05 (m, 1H), 7.98–8.00 (m, 1H), 7.64–7.71 (m, 3H), 7.44–7.49 (m, 1H), 7.32–7.36 (m, 1H), 7.16–7.18 (m, 1H), 4.75 (q, 1H, J=6.5 Hz), 2.72 (s, 3H), 1.28 (d, 3H, J=6.5 Hz). ESI-MS (m/z): Calcd. for C20H20N2O3S3: 433.6 (M+H); found: 433.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customre-acidified with TFA and purified
  3. customC18-HPLC (10–80% CH3CN in H2O (0.1% TFA) over 30 min)

Sources & evidence

ORD record
ord-e734ff83ef63429e992425a522d3fa7a
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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