Trifluoroacetic acid methylene chloride → HCID 11330652, compound

HRID 29451Notes

Reaction equation

HRID 29451 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[S:31][C:32]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:33]=4[N:34]=3)=[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.C(Cl)Cl>>[CH3:9][CH:8]([CH3:10])[C@H:7]([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]3[S:31][C:32]4[CH:38]=[CH:37][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:35][C:33]=4[N:34]=3)=[O:29])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])[C:6]([OH:43])=[O:5]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68714729(S)-3-methyl-2-{4'-[(5-trifluoromethyl-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester

Product 1

HCID 11330652HCID 11330652, compoundYield 94.6%

Procedure

To (S)-3-methyl-2-{4′-[(5-trifluoromethyl-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester (210 mg) was added 3 mL of TFA/CH2Cl2 (1:1). The solution was stirred at room temperature for 3 h. The solvents were removed under vacuum and the residue was triturated with ether. Filtration gave 181 mg of (S)-3-methyl-2-{4′-[(5-trifluoromethyl-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid as a yellow solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 0.83 (dd, J=12.63, 6.82 Hz, 6 H) 1.92-2.00 (m, 1 H) 3.56 (dd, J=9.35, 6.06 Hz, 1 H) 7.80-7.86 (m, 4 H) 7.88-7.92 (m, 2 H) 7.97 (dd, J=8.59, 1.52 Hz, 1 H) 8.05-8.07 (m, 1 H) 8.09 (d, J=2.78 Hz, 1 H) 8.49 (s, 1 H) 8.57 (d, J=8.59 Hz, 1 H) 11.41 (s, 1 H).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was triturated with ether
  3. filtrationFiltration

Sources & evidence

ORD record
ord-d018983ba81f49da8d825bbbe3ab247e
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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