Trifluoroacetic acid → 3,5-Dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamide

HRID 1889641Notes

Reaction equation

HRID 1889641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH2:21][N:22]([CH2:35][CH:36]([CH3:38])[CH3:37])[S:23]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[C:27]=2[OH:34])(=[O:25])=[O:24])[CH:20]=1)[CH2:5][N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:28]1[C:27]([OH:34])=[C:26]([S:23]([N:22]([CH2:21][C:19]2[CH:18]=[C:4]([CH2:5][NH:6][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:3]=[C:2]([Cl:1])[CH:20]=2)[CH2:35][CH:36]([CH3:37])[CH3:38])(=[O:25])=[O:24])[CH:31]=[C:30]([Cl:32])[CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58531453tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate

Product 1

HCID 585315243,5-Dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamideYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate (0.23 g, 0.38 mmol) in methylene chloride (5 mL) was added TFA (0.87 mL, 11.3 mmol). The reaction mixture was stirred at rt for 2 h., concentrated and the residue was partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated to give the desired product as white solid (0.18 g, 92%). 1H NMR (CD3OD): δ 7.45 (d, J=2.8 Hz, 2H), 7.40 (s, 2H), 7.37 (s, 1H), 7.31 (d, J=2.8 Hz, 1H), 4.57 (s, 2H), 4.07 (s, 2H), 3.04 (d, J=7.2 Hz, 2H), 2.80 (d, J=7.2 Hz, 2H), 2.00 (m, 1H), 1.68 (m, 1H), 1.00 (d, J=6.6 Hz, 6H), 0.76 (d, J=6.6 Hz, 6H); MS (ESI): (M+H)+=507.22, 509.21.

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between saturated NaHCO3 solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f139fadde65949fdbb90665035f403d9
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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