Tetrahydrofuran → (R)-N-((S)-(3-fluoro-4-methoxyphenyl)(1-methyl-1H-imidazol-5-yl)methyl)-2-methylpropane-2-sulfinamide

HRID 1051387Notes

Reaction equation

[CH3:1][C:2]([S@:5](/[N:7]=[CH:8]/[C:9]1[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=1)=[O:6])([CH3:4])[CH3:3].C1COCC1.[F:20][C:21]1[CH:22]=[C:23]([Mg]Br)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>O>[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[F:20][C:21]1[CH:22]=[C:23]([C@@H:8]([C:9]2[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=2)[NH:7][S@@:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 128 (1.444 g, 6.770 mmol) and THF (20 mL) was cooled to −10° C., and (3-fluoro-4-methoxyphenyl)magnesium bromide (2.717 g, 11.85 mmol) was added via addition funnel. The reaction was stirred at −10° C. for 1 h. Water was added, and the mixture was extracted with EtOAc. The organic layer was concentrated, and the resulting residue was purified by reverse phase chromatography (eluting with 0-65% MeCN/water) to afford 0.203 g (8.83%) of (R)—N#R)-(3-fluoro-4-methoxyphenyl)(1-methyl-1H-imidazol-5-yl)methyl)-2-methylpropane-2-sulfinamide (130a) and 315 mg (13.71%) of (R)—N—((S)-(3-fluoro-4-methoxyphenyl)(1-methyl-1H-imidazol-5-yl)methyl)-2-methylpropane-2-sulfinamide (1306).

Workup

extractionthe mixture was extracted with EtOAc
concentrationThe organic layer was concentrated
customthe resulting residue was purified by reverse phase chromatography (eluting with 0-65% MeCN/water)

Sources & evidence

ORD record: ord-a84d612c481943bf912597739cb90484
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388171B2

Reaction notes

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