4-Toluenesulfonyl chloride → 3,5-Dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxy-N-(3-((4-methylphenylsulfonamido)methyl)benzyl)benzenesulfonamide

HRID 1889623Notes

Reaction equation

HRID 1889623 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.[NH2:19][CH2:20][C:21]1[CH:22]=[C:23]([CH:53]=[CH:54][CH:55]=1)[CH2:24][N:25]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)=[CH:41][CH:40]=1)[S:26]([C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[C:30]=1[OH:37])(=[O:28])=[O:27]>C(Cl)Cl>[Cl:36][C:31]1[C:30]([OH:37])=[C:29]([S:26]([N:25]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46]3[CH:47]=[CH:48][C:49]([F:52])=[CH:50][CH:51]=3)=[CH:41][CH:40]=2)[CH2:24][C:23]2[CH:53]=[CH:54][CH:55]=[C:21]([CH2:20][NH:19][S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:22]=2)(=[O:28])=[O:27])[CH:34]=[C:33]([Cl:35])[CH:32]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 58531351N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxybenzenesulfonamide

Product 1

HCID 666166573,5-Dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxy-N-(3-((4-methylphenylsulfonamido)methyl)benzyl)benzenesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-methylbenzene-1-sulfonyl chloride (25 mg, 0.13 mmol) in CH2Cl2 (3 mL) were added Et3N (0.10 ml, 075 mmol) and N-(3-(aminomethyl)benzyl)-3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxybenzenesulfonamide (70 mg, 0.13 mmol). The reaction mixture was stirred at rt. under nitrogen for 2 h. The mixture was concentrated and dissolved in MeOH, purified by preparative HPLC. The fractions containing the desired product were combined, concentrated and lyophilized to give white solid (52 mg, 58%).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in MeOH
  3. custompurified by preparative HPLC
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-62fe431dcf634b5491e02eb8d3b9f75c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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