Thiophenol → HCID 118130106, compound

HRID 1778156Notes

Reaction equation

HRID 1778156 reaction equation
S(C1C=CC([N+]([O-])=O)=CC=1)(O)(=O)=O.[CH3:14][S@@:15]([CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[NH:17])=[O:16].C1(S)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:14][S@@:15]([CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[NH:17])=[O:16]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 131734806HCID 131734806, compound

Product 1

HCID 118130106HCID 118130106, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
46 °C

Procedure

A mixture of (R)-{[3-(S-methylsulfonimidoyl)propoxy]methyl}benzene nosylate (0.51 g, 1.24 mmol), PhSH (0.22 g, 1.98 mmol) and Cs2CO3 (0.73 g, 2.23 mmol) in CH3CN (10 mL) was stirred at 46° C. overnight, filtered, concentrated, and purified by chromatography (EtOAc/MeOH) to give the title compound (0.26 g, >99% ee).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by chromatography (EtOAc/MeOH)

Sources & evidence

ORD record
ord-6574e74d1aba42ed8e2d97f8f046c359
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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