Cesium carbonate → HCID 123493894, compound

HRID 2369814Notes

Reaction equation

HRID 2369814 reaction equation
[C:1]1([C@H:7]2[CH2:11]OS(=O)(=O)[N:8]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:21][N:22]([S:23]([C:26]1[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)(=[O:25])=[O:24])[CH2:11][C@@H:7]([NH:8][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 232993N-Methyl-4-nitrobenzenesulfonamideHCID 11243499(4S)-4-Phenyl-1,2,3-oxathiazolidine-2,2-dioxide-3-carboxylic acid t-butyl ester, min. 97%

Product 1

HCID 123493894HCID 123493894, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (45)-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (1 g; 3.34 mmol), N-methyl-4-nitrobenzenesulfonamide (722 mg; 3.34 mmol), and Cs2CO3 (0.40 ml; 5.01 mmol) were dissolved in CH3CN (25 ml), and stirred overnight. The reaction mixture was filtered, washed with H2O (50 ml), and dried under vacuum to provide the desired intermediate (1.12 g; 77%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with H2O (50 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-13f6408fac7e4dba9226ffcd76f0d525
Source dataset
uspto-grants-2014_04
Patent number
US08710044B2

Reaction notes

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