Sodium Iodide → N-(2-Thioacetyl-3-chlorobenzoyl)-N-cyclopentylglycine
Reaction equation
C([O:5][C:6](=[O:26])[CH2:7][N:8]([C:14](=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[C:22](=[S:24])[CH3:23])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.[I-].[Na+].Cl[Si](C)(C)C>CC#N>[C:22]([C:16]1[C:17]([Cl:21])=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([N:8]([CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:7][C:6]([OH:26])=[O:5])=[O:25])(=[S:24])[CH3:23]Participants
5
Conditions
- Temperature
- 55 °C
Procedure
N-(2-Thioacetyl-3-chlorobenzoyl)-N-cyclopentylglycine t-butyl ester (20.6 g, 0.05 mol) was dissolved in 150 ml CH3CN. Sodium iodide (11.3 g, 0.075 m) was then added. The resulting slurry was covered with nitrogen and warmed to 55° C. Chlorotrimethylsilane (8.15 g, 0.075 m) was then added in one portion. The reaction was stirred 30 minutes at 55° C. under nitrogen atmosphere. The heat source was removed and the reaction cooled to room temperature in an ice bath. Water (60 ml) and CH2Cl2 (100 ml) were then added. The aqueous layer was quickly withdrawn and the organic layer washed 2×75 ml H2O, 2×75 ml Na2S2O3 and 2×75 ml brine. The organic layer was then dried (MgSO4), filtered and concentrated to yield a dark yellow oil.
Workup
- customThe heat source was removed
- temperaturethe reaction cooled to room temperature in an ice bath
- additionWater (60 ml) and CH2Cl2 (100 ml) were then added
- customThe aqueous layer was quickly withdrawn
- washthe organic layer washed 2×75 ml H2O, 2×75 ml Na2S2O3 and 2×75 ml brine
- dry with materialThe organic layer was then dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto yield a dark yellow oil
Sources & evidence
- ORD record
- ord-4ef6e783f3ae49f0b663a86b8846523c
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04347246
Reaction notes
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