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

HRID 1889666Notes

Reaction equation

HRID 1889666 reaction equation
[Cl:1][C:2]1[C:3]([OH:37])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[CH:36]=[CH:35][C:25]([CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[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>[NH2:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[S:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[OH:37])(=[O:11])=[O:10])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66616495tert-Butyl 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

Product 1

HCID 58531430N-(4-(Aminomethyl)benzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate (569 mg, 1.00 mmol) in methylene chloride (9 mL) was added TFA (3 mL). The reaction mixture was stirred at rt for 2 h, and then concentrated. The residue was dissolved in with methylene chloride (100 mL) and washed with saturated aq sodium bicarbonate solution, brine, dried over MgSO4, and concentrated to give the title compound (446 mg, 95%) as a tan solid. MS (ESI): m/z 468.9 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in with methylene chloride (100 mL)
  3. washwashed with saturated aq sodium bicarbonate solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc380e0d6c29402bbd065a61501117ba
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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