4-Fluorobenzenesulfonyl chloride → Methyl 2-(4-(4-(3,4-dichlorobenzamido)phenoxy)-3-((4-fluorophenyl-sulfonamido)methyl)phenyl)acetate

HRID 453483Notes

Reaction equation

HRID 453483 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:12][CH:11]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[Cl:24])[C:17]([NH:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:4][C:3]=2[CH2:2][NH:1][S:39]([C:36]2[CH:37]=[CH:38][C:33]([F:32])=[CH:34][CH:35]=2)(=[O:41])=[O:40])=[CH:15][CH:14]=1)=[O:26]

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68469006HCID 68469006, compound

Product 1

HCID 68463196Methyl 2-(4-(4-(3,4-dichlorobenzamido)phenoxy)-3-((4-fluorophenyl-sulfonamido)methyl)phenyl)acetateYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step H (30 mg, 0.065 mmol) was diluted with methylene chloride (1 mL) followed by the addition of 4-fluorobenzene-1-sulfonyl chloride (15 mg, 0.078 mmol) and DIEA (0.024 mL, 0.14 mmol). After stirring the reaction for 4 hours, the reaction mixture was placed directly onto a preparative tlc plate 0.5 mm and eluted with hexanes:ethyl acetate (3:1) to yield 30 mg of methyl 2-(4-(4-(3,4-dichlorobenzamido)phenoxy)-3-((4-fluorophenyl-sulfonamido)methyl)phenyl)acetate.

Workup

  1. customthe reaction for 4 hours
  2. washeluted with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-b59579895f7a424db89a398d9b7bd508
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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