4-Fluorobenzenesulfonyl chloride → methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(4-fluoro-N-methylphenylsulfonamido)ethyl)phenoxy)acetate

HRID 68600Notes

Reaction equation

HRID 68600 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([C:9]2[CH:20]=[C:19]([CH:21]([NH:23][CH3:24])[CH3:22])[CH:18]=[CH:17][C:10]=2[O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1.CCN(C(C)C)C(C)C.[F:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1>C1COCC1>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:4]=[C:5]([C:9]2[CH:20]=[C:19]([CH:21]([N:23]([CH3:24])[S:43]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)(=[O:45])=[O:44])[CH3:22])[CH:18]=[CH:17][C:10]=2[O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67527946Methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(methylamino)ethyl)phenoxy)acetate

Product 1

HCID 70804820methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(4-fluoro-N-methylphenylsulfonamido)ethyl)phenoxy)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(methylamino)ethyl)phenoxy)acetate (18) (100 mg) in 2 mL of THF, was added DIEA (105 mg), and 4-fluorobenzene-1-sulfonyl chloride (87 mg). The reaction mixture was stirred at room temperature for 1 hr and then purified via silica gel chromatography (25% EtOAc/hexane) to give methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(4-fluoro-N-methylphenylsulfonamido)ethyl)phenoxy)acetate (19) which was carried directly to the next step.

Workup

  1. custompurified via silica gel chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-2f52b231d3224dd2bb82925af0018e8f
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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