4-Toluenesulfonyl chloride → HCID 67410578, compound
Reaction equation
[CH2:1]([C:3]1([C@@H:7]([OH:11])[CH2:8][CH2:9]O)[CH2:6][CH2:5][CH2:4]1)[CH3:2].[OH-].[Na+].S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C:25]1([N:31]2[C:35]([SH:36])=[N:34][N:33]=[N:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([C:3]1([C@@H:7]([OH:11])[CH2:8][CH2:9][S:36][C:35]2[N:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:32]=[N:33][N:34]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
To a solution of (1S)-1-(1-ethylcyclobutyl)-propane-1,3-diol (8.90 g) in toluene (110 mL) were added tetrabutylammonium chloride (1.56 g) and a 2N aqueous sodium hydroxide solution (170 mL). At an inner temperature about 25° C., tosyl chloride (11.3 g) was added to the reaction solution, which was stirred at 25° C. for 1 hour. 1-Phenyl-1H-tetrazol-5-thiol (11.0 g) was added to the reaction solution, which was stirred at 60° C. for 1 hour. After cooling, water was added to the reaction solution, which was separated. The water layer was extracted with t-butyl methyl ether. The mixed organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (17.9 g) having the following physical data.
Workup
- stirringwas stirred at 60° C. for 1 hour
- temperatureAfter cooling
- customwas separated
- extractionThe water layer was extracted with t-butyl methyl ether
- washThe mixed organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a5eb043886654f679f5c5e0a71c2a6e6
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402605B2
Reaction notes
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