Triacetoxyperiodinane → HCID 9979610, compound

HRID 2214108Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:22][CH:23]2[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:22][CH:23]2[CH2:27][CH2:26][C:25](=[O:28])[CH2:24]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-hydroxy-cyclopentyl)-N-pyrazin-2-yl-propionamide (prepared as in Example 38, 60 mg, 0.142 mmol) in methylene chloride (10 mL) was treated with Dess-Martin periodinane (132.5 mg, 0.312 mmol). The reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was then diluted with methylene chloride (10 mL) and washed with a 1M aqueous citric acid solution (10 mL). The pH of the aqueous layer was adjusted to 5. The aqueous layer was then extracted with methylene chloride (20 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50–100% ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-N-pyrazin-2-yl-propionamide (45 mg, 75%) as an off-white solid.

Workup

washwashed with a 1M aqueous citric acid solution (10 mL)
extractionThe aqueous layer was then extracted with methylene chloride (20 mL)
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-71cedd3a89a2457b83fb408ef407ecee
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105671B2

Reaction notes

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