Hydrochloric Acid → HCID 10590341, compound

HRID 656273Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].Cl>ClCCl.O>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 8-1 (1 g) was dissolved in anhydrous dichloromethane and the solution was cooled to 0° C. To the solution was added triethylamine (630 μl) and methanesulfonyl chloride (350 μl) in order and the mixture was stirred at room temperature for 24 hours. After confirming the completion of the reaction using TLC, the resulting mixture was neutralized with hydrochloric acid solution, diluted with water, and then extracted three times with dichloromethane. The extracted organic layer was washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then dried under reduced pressure. The obtained residue was purified by column-chromatography (hexane/ethyl acetate=2/1) to yield the compound 8-2 (1.28 g, 95%) as a white solid.

Workup

extractionextracted three times with dichloromethane
washThe extracted organic layer was washed with water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customdried under reduced pressure
customThe obtained residue was purified by column-chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-1e7556a6b4a64913a8d67407b5d2279a
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071650B2

Reaction notes

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