4-Fluorobenzyl chloride → HCID 21098731, compound

HRID 1351312Notes

Reaction equation

HRID 1351312 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH2:9][N:10]([CH3:23])[S:11]([C:14]2[CH:18]=[C:17]([C:19](=[O:21])[CH3:20])[S:16][C:15]=2[NH2:22])(=[O:13])=[O:12])=[CH:4][CH:3]=1.[OH-].[Na+].FC1C=CC(CCl)=CC=1.[F:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1>C(OCC)(=O)C.O1CCCC1>[C:19]([C:17]1[S:16][C:15]([NH:22][C:41](=[O:42])[C:40]2[CH:44]=[CH:45][C:37]([F:36])=[CH:38][CH:39]=2)=[C:14]([S:11](=[O:13])(=[O:12])[N:10]([CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[OH:24])[CH3:23])[CH:18]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 96024-Fluorobenzyl chlorideHCID 14798Sodium Hydroxide3×HCID 678794-Fluorobenzoyl chloride2×HCID 86600997HCID 86600997, compound

Product 1

HCID 21098731HCID 21098731, compound

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of 5-acetyl-2-amino-thiophene-3-sulfonic acid [2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-amide (the compound of Preparation Example 99) (120 mg) in ethyl acetate-tetrahydrofuran (4:1) (30 mL) was added an aqueous solution (10 mL) of 2N sodium hydroxide. After stirring vigorously at room temperature, 4-fluorobenzyl-chloride (51 mg) was added. After 30 minutes, an aqueous solution (10 mL) of 2N sodium hydroxide, then 4-fluorobenzoyl-chloride (100 mg) were added, and the solution was stirred for 30 minutes. In addition, an aqueous solution (10 mL) of 2N sodium hydroxide, then 4-fluorobenzoyl-chloride (100 mg) were added. After stirring for 30 minutes, extraction was carried out by adding ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate. Purification was carried out by purification with silica gel column chromatography (hexane/ethyl acetate), and the title compound (59 mg) was obtained as yellow solids.

Workup

  1. stirringthe solution was stirred for 30 minutes
  2. stirringAfter stirring for 30 minutes
  3. extractionextraction
  4. additionby adding ethyl acetate
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. customPurification
  7. customwas carried out by purification with silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8b22718dd42646838dc8da64441d108b
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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