Cesium carbonate → tert-Butyl (3-{[(3-nitrobenzyl)thio]methyl}phenyl)carbamate

HRID 541930Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[N+:7]([C:10]1[CH:11]=[C:12]([CH2:16][SH:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].CS(O[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:25]=1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[N+:7]([C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][S:17][CH2:23][C:24]1[CH:25]=[C:26]([NH:30][C:31](=[O:32])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH:27]=[CH:28][CH:29]=1)([O-:9])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of cesium carbonate (0.57 g, 1.8 mmol) in N,N-dimethylformamide (1.8 mL) at 0° C. was treated with (3-nitrophenyl)methanethiol (0.22 mL, 1.6 mmol) dropwise and stirred at 0° C. for 10 min. The reaction mixture was treated with a solution of 3-[(tert-butoxycarbonyl)amino]benzyl methanesulfonate (0.41 g, 1.3 mmol) in N,N-dimethylformamide (2.4 mL) dropwise and stirred at 0° C. for 30 min. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (40 mL) and brine (20 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and evaporated to a crude brown oil. This material was purified by flash column chromatography to give the desired product (0.42 g, 84% for 2 steps) as a yellow oil. LCMS for C19H22N2O4SNa (M+Na)+: m/z=396.7.

Workup

stirringstirred at 0° C. for 30 min
washwashed with water (40 mL) and brine (20 mL)
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated to a crude brown oil
customThis material was purified by flash column chromatography

Sources & evidence

ORD record: ord-90527d0cc7eb4187b97816ead7e1b4a8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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