Benzyl Bromide → methyl 3-(4-benzyloxyazepan-1-yl)Sulfonyl-4-bromo-benzoate

HRID 1754301Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([N:15]1[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13].[H-].[Na+].Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH4+].[Cl-]>CN(C=O)C>[CH2:26]([O:22][CH:18]1[CH2:19][CH2:20][CH2:21][N:15]([S:12]([C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=2[Br:1])[C:6]([O:8][CH3:9])=[O:7])(=[O:14])=[O:13])[CH2:16][CH2:17]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of methyl 4-bromo-3-(4-hydroxyazepan-1-yl)sulfonyl-benzoate (1.00 g, 2.55 mmol, 1.00 Eq) in DMF (15 mL), was added NaH (153.00 mg, 3.82 mmol, 1.50 Eq) in portions at 0° C. under N2. The mixture was stirred at 25° C. for 30 min. Then bromomethylbenzene (654.19 mg, 3.82 mmol, 1.50 Eq) was added and stirred at 25° C. for 16 hours. TLC showed the reaction was completed. The mixture was poured into NH4Cl aqueous and extracted with EA. The combined organic phase was washed with saturated brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (eluting with PE/EA=10/1, 2/1) to afford methyl 3-(4-benzyloxyazepan-1-yl)Sulfonyl-4-bromo-benzoate (550.00 mg, 1.14 mmol, 44.71% yield) as white solid. LCMS: 482/484 [M+1].

Workup

stirringstirred at 25° C. for 16 hours
extractionextracted with EA
washThe combined organic phase was washed with saturated brine
dry with materialdried with anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuum
customThe residue was purified by silica gel chromatography (eluting with PE/EA=10/1, 2/1)

Sources & evidence

ORD record: ord-a85a2fe59f554313bd67671f80530831
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169212B2

Reaction notes

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