(RS)-S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulfoximide → (RS)-S-(4-aminophenyl)-N-(2-methoxy-acetyl)-S-methylsulphoximide

HRID 1169721Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:18])(=[N:12][C:13](=[O:17])[CH2:14][O:15][CH3:16])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:18])(=[N:12][C:13](=[O:17])[CH2:14][O:15][CH3:16])=[O:11])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 24 °C

Procedure

107 mg (0.39 mmol) (RS)—S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulphoximide is dissolved in 13.6 ml ethanol and treated with 40 mg palladium on activated charcoal (10% Pd). The mixture is stirred under hydrogen at normal pressure for 60 minutes at 24° C. The catalyst is filtered off and the solution concentrated. After chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 50 mg (53%) of the desired product is obtained.

Workup

filtrationThe catalyst is filtered off
concentrationthe solution concentrated
customAfter chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate))

Sources & evidence

ORD record: ord-60f05c1c629647e28aa98ae310dfe87f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

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