Methanol → HCID 68784885, compound

HRID 2266034Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([C:8](=[N:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH3:9])[CH:5]=[C:4]([F:17])[C:3]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20].[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([NH:10][S:11]([C:13]([CH3:16])([CH3:14])[CH3:15])=[O:12])[CH3:9])[CH:5]=[C:4]([F:17])[C:3]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20]

Participants

Conditions

Temperature: -48 °C

Procedure

To a solution of N-(4-acetyl-2,6-difluoro-phenyl)-methanesulfonamide (1.84 g, 7.38 mmol) and (R)-(+)-2-methyl-2-propanesulfinamide (1.07 g, 8.86 mL) in THF (15 mL) was added dropwise Ti(OEt)4 (2.61 mL, 12.6 mmol) at room temperature. The mixture was stirred overnight at 90° C. The mixture cooled to room temperature and then was added brine. After the mixture was extracted three times with EtOAc, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by chromatography to yield N-{2,6-difluoro-4-[1-(2-methyl-propane-2-sulfinylimino)-ethyl]-phenyl}-methanesulfonamide (2.2 g, 85%). To a solution of N-{2,6-difluoro-4-[1-(2-methyl-propane-2-sulfinylimino)-ethyl]-phenyl}-methanesulfonamide (2.2 g, 6.24 mmol) in THF (20 mL) was added portionwise NaBH4 (944 mg, 24.9 mmol) dissolved in THF (2 mL) at −48° C. The mixture was stirred for 10 hours at −48° C. room temperature, and then CH3OH was added dropwise until gas was no longer evolved. The mixture was concentrated under reduced pressure, and then was purified by chromatography to afford N-{2,6-difluoro-4-[1-(2-methyl-propane-2-sulfinylamino)-ethyl]-phenyl}-methanesulfonamide (1.89 g, 50%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customwas purified by chromatography

Sources & evidence

ORD record: ord-0e0bf6f9207341c59e5e63e20a02c35c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858621B2

Reaction notes

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