p-Toluenesulfonyl azide → 3-azido-N-(tert-butyl)-5-chlorothiophene-2-sulfonamide

HRID 601296

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Cl:14])=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]C(CC)C.S([N:30]=[N+:31]=[N-:32])(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[N:30]([C:13]1[CH:12]=[C:11]([Cl:14])[S:10][C:9]=1[S:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:7])=[O:8])=[N+:31]=[N-:32]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of Example 311A (1.01 g, 3.99 mmol) in tetrahydrofuran (32 mL) at −78° C. was treated with dropwise addition of sec-BuLi (1.4 M in hexane, 2.1 equivalents). The reaction was warmed to −20° C. and stirred for 30 minutes, treated with a solution of tosyl azide (1.1 equivalent) in tetrahydrofuran (7 mL) at −20° C., stirred at 25° C. for 18 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with a gradient of 30% dichloromethane in hexane to 100% dichloromethane to give approximately a 2:1 mixture of starting material to the title compound.

Workup

stirringstirred at 25° C. for 18 hours
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel
washeluting with a gradient of 30% dichloromethane in hexane to 100% dichloromethane
customto give approximately

Sources & evidence

ORD record: ord-7efb5ee33b4c451987074e00ee74054e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Linked notes

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