Trifluoroacetic acid methylene chloride → (S)-2-{4'-[(4-Methoxy-3,5-dimethyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid

HRID 29427Notes

Reaction equation

HRID 29427 reaction equation
C([O:5][C:6](=[O:43])[C@@H:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]3[O:31][C:32]4[CH:39]=[CH:38][C:37]([CH3:40])=[C:36]([O:41][CH3:42])[C:33]=4[C:34]=3[CH3:35])=[O:29])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.ClCCl>>[CH3:42][O:41][C:36]1[C:33]2[C:34]([CH3:35])=[C:30]([C:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([C:18]4[CH:19]=[CH:20][C:15]([S:12]([NH:11][C@@H:7]([CH:8]([CH3:9])[CH3:10])[C:6]([OH:43])=[O:5])(=[O:13])=[O:14])=[CH:16][CH:17]=4)=[CH:22][CH:23]=3)=[O:29])[O:31][C:32]=2[CH:39]=[CH:38][C:37]=1[CH3:40]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68713923(S)-2-{4'-[(4-methoxy-3,5-dimethyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester

Product 1

HCID 44404503(S)-2-{4'-[(4-Methoxy-3,5-dimethyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acidYield 88.2%

Procedure

To 80 mg of (S)-2-{4′-[(4-methoxy-3,5-dimethyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester was added 2 mL of TFA/dichloromethane (1:1) and the solution was stirred at room temperature for 3 h. When the reaction was done, the solvent was removed under vacuum and the residue was triturated with acetonitrile. Filtration of the suspension gave 64 mg of (S)-2-{4′-[(4-methoxy-3,5-dimethyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=12.4, 6.8 Hz, 6 H) 2.0 (m, 1 H) 2.3 (s, 3 H) 2.7 (s, 3 H) 3.6 (dd, J=9.3, 5.8 Hz, 1 H) 3.8 (s, 3 H) 7.4 (m, 2 H) 7.8 (d, J=8.8 Hz, 2 H) 7.9 (m, 4 H) 8.0 (d, J=8.8 Hz, 2 H) 8.1 (d, J=9.3 Hz, 1 H) 10.5 (s, 1 H).

Workup

  1. customthe solvent was removed under vacuum
  2. customthe residue was triturated with acetonitrile
  3. filtrationFiltration of the suspension

Sources & evidence

ORD record
ord-04748ca406794cdd936667335c06b69b
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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