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

HRID 29382Notes

Reaction equation

HRID 29382 reaction equation
C([O:5][C:6](=[O:45])[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]([Cl:40])=[C:36]([O:41][CH:42]([CH3:44])[CH3:43])[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>>[Cl:40][C:37]1[CH:38]=[CH:39][C:32]2[O:31][C:30]([C:28]([NH:27][C:24]3[CH:23]=[CH:22][C:21]([C:18]4[CH:17]=[CH:16][C:15]([S:12]([NH:11][C@@H:7]([CH:8]([CH3:9])[CH3:10])[C:6]([OH:45])=[O:5])(=[O:13])=[O:14])=[CH:20][CH:19]=4)=[CH:26][CH:25]=3)=[O:29])=[C:34]([CH3:35])[C:33]=2[C:36]=1[O:41][CH:42]([CH3:44])[CH3:43]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68715589(S)-2-{4'-[(5-chloro-4-isopropoxy-3-methyl-benzofuran-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester

Product 1

HCID 11330861(S)-2-{4'-[(5-Chloro-4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acidYield 82%

Procedure

To 160 mg of (S)-2-{4′-[(5-chloro-4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester was added 3 mL of TFA/dichloromethane (1:1) and the solution was stirred at room temperature for 9 h. When the reaction was done, the solvents were removed under vacuum and the residue was triturated with acetonitrile. The mixture was freeze-dried to yield 120 mg (77% yield) of (S)-2-{4′-[(5-chloro-4-isopropoxy-3-methyl-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) 1.3 (d, J=6.1 Hz, 6 H) 1.9 (m, 1 H) 2.7 (s, 3 H) 3.6 (dd, J=9.3, 6.1 Hz, 1 H) 4.7 (m, 1 H) 7.5 (d, J=8.8 Hz, 1 H) 7.6 (m, 1 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) 10.6 (s, 1 H) 12.6 (s, 1 H).

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was triturated with acetonitrile
  3. customThe mixture was freeze-dried

Sources & evidence

ORD record
ord-d507c471b8cd49bfbb2c7dfcb29c9b0a
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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