Iodine → (R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

HRID 989497Notes

Reaction equation

[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[I:24](O)(=O)(=O)=O.II.S(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[I:24][C:4]1[CH:3]=[CH:2][C:1]([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(+,−) Cis-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide (1.8 g, 6.7 mmol, prepared in example 16) was dissolved in 20 mL of glacial acetic acid and 0.7 mL (7.1 mmol) of concentrated sulfuric acid added followed by 2 mL of water. To this solution was added periodic acid (0.35 g, 1.6 mmol) and iodine (0.77 g, 3.0 mmol). The resulting mixture was heated to 60° C. for 3 hours. The reaction was cooled to room temperature and 20 mL of a 10% aqueous solution of sodium bisulfite was added. The product was extracted into ethyl acetate then washed with water, dilute sodium bicarbonate, and dried over magnesium sulfate. Filtered and concentrated in vacuo to 2.2 g of crude yellow oil. This oil was purified by reverse phase chromatography to give 341 mg (13%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Workup

temperatureThe reaction was cooled to room temperature
extractionThe product was extracted into ethyl acetate
washthen washed with water, dilute sodium bicarbonate
dry with materialdried over magnesium sulfate
filtrationFiltered
concentrationconcentrated in vacuo to 2.2 g of crude yellow oil
customThis oil was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-9722809d6a9344b38a783b869c2e2339
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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