Trifluoroacetic acid → N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxybenzenesulfonamide

HRID 1889622Notes

Reaction equation

HRID 1889622 reaction equation
[Cl:1][C:2]1[C:3]([OH:44])=[C:4]([S:9]([N:12]([CH2:28][C:29]2[CH:30]=[C:31]([CH:41]=[CH:42][CH:43]=2)[CH2:32][NH:33]C(=O)OC(C)(C)C)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:33][CH2:32][C:31]1[CH:30]=[C:29]([CH:43]=[CH:42][CH:41]=1)[CH2:28][N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:18][CH:19]=1)[S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:44])(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58531654tert-Butyl 3-((3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

Product 1

HCID 58531351N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxybenzenesulfonamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate (0.98 g, 1.48 mmol) in CH2Cl2 (15 mL) was added TFA (2.28 mL, 29.6 mmol). The reaction mixture was stirred at rt for 3 h. The mixture was concentrated and the residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer (clear solution) was washed with brine, dried over MgSO4 and concentrated to give white solid (0.65 g, 70%). 1H NMR (DMSO-d6): δ 8.50 (bs, 1H), 7.52 (s, 1H), 7.34 (d, J=2.8 Hz, 1H), 7.2.9 (d, J=2.8 Hz, 1H), 7.26-7.21 (m, 4H), 7.12-7.08 (m, 3H), 6.97-6.94 (m, 2H), 6.80 (d, J=6.8 Hz, 2H), 4.41 (s, 2H), 4.32 (s, 2H), 3.94 (s, 2H); MS (ESI): (M+H)+=561.1.

Workup

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

Sources & evidence

ORD record
ord-c0ed4a51a3dc42369c3ad542f9ddc463
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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