Sodium sulfate decahydrate → N-[4-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-(hydroxymethyl)phenyl]methanesulfonamide

HRID 230592Notes

Reaction equation

[Li].[H-].[C:3]([S@:7]([NH:9][C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[C:16]([CH:22]=1)[C:17](OCC)=[O:18])[CH3:11])=[O:8])([CH3:6])([CH3:5])[CH3:4].[F-].[K+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:3]([S@:7]([NH:9][C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[C:16]([CH2:17][OH:18])[CH:22]=1)[CH3:11])=[O:8])([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of lithium alminium hydride (1.6 g, 43 mmol) in tetrahydrofuran (THF) (50 ml) was added a solution of ethyl 5-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-[(methylsulfonyl)amino]benzoate (4.2 g, 11 mmol) in tetrahydrofuran (THF) (100 ml) at 0° C. After being stirred for 3 hours at 0° C., potassium fluoride and sodium sulfate decahydrate were added. After being stirred for 5 hours, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give 3.6 (97% yield) of the title compound as slightly yellow oil. MS (ESI) m/z 391 [M+H]+, 389 [M−H]−.

Workup

stirringAfter being stirred for 5 hours
filtrationthe reaction mixture was filtered
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3487f9bb3822493791449ce751f850a6
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566739B2

Reaction notes

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