Sodium Iodide → N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine

HRID 325490Notes

Reaction equation

C([O:5][C:6](=[O:27])[CH2:7][N:8]([C:14](=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[S:22][C:23](=[O:25])[CH3:24])[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:23]([S:22][C:16]1[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH2:7][C:6]([OH:27])=[O:5])=[O:26])(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 55 °C

Procedure

N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine t-butyl ester (16.7 g, 0.047 mole) was dissolved in 100 ml CH3CN. Sodium iodide (9.6 g, 0.064 mole) was then added. The resulting slurry was covered with a nitrogen atmosphere and warmed slowly to 55° C. Chlorotrimethylsilane (6.9 g, 0.0641 mole) was then added in one portion. The reaction was stirred 30 minutes at 50°-55° C. The heat source was then removed and the reaction cooled to room temperature with an ice bath. Water (60 ml) and CH2Cl2 (100 ml) were then added. The reaction mixture was transferred to a separatory funnel and the aqueous layer quickly withdrawn. The organic was washed 2×50 ml H2O, 3×75 ml Na2S2O3, 2×100 ml brine, dried (MgSO4), filtered and concentrated in vacuo to give 15.9 g of an orange oil.

Workup

customThe heat source was then removed
temperaturethe reaction cooled to room temperature with an ice bath
additionWater (60 ml) and CH2Cl2 (100 ml) were then added
customThe reaction mixture was transferred to a separatory funnel
customthe aqueous layer quickly withdrawn
washThe organic was washed 2×50 ml H2O, 3×75 ml Na2S2O3, 2×100 ml brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bb3538ecb35d459ba74123fa07b8e3a6
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04440941

Reaction notes

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