Hydrochloric Acid → HCID 86732221, compound

HRID 930390Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:22][S@@:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])([CH2:12]/[C:13](=N/N(C)C)/[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11].Cl.C1C[O:33]CC1>>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:22][S@@:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])([CH2:12][C:13](=[O:33])[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8028Tetrahydrofuran

HCID 90372751HCID 90372751, compound

Product 1

HCID 86732221HCID 86732221, compound

Procedure

A solution of (R)-N-((Z)-2-(2,3-difluorophenyl)-4-(2,2-dimethylhydrazono)-1,5,5,5-tetrafluoropentan-2-yl)-2-methylpropane-2-sulfinamide (9.0 g, 20.86 mmol) in THF (10 mL) was treated with hydrogen chloride, 2M aq. solution (10.43 mL, 20.86 mmol). The mixture was stirred at ambient temperature for 26 h. LCMS detected formation of desired product and trace of starting material. The reaction was quenched with saturated NaHCO3 solution and then extracted with EtOAc (2×). The organic extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by silica gel column (0-50% EtOAc/hexane) to afford 5.0 g of (R)-N-(2-(2,3-difluorophenyl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide as light yellow solid (91% purity). MS m/z=408.0 [M+H+H2O]+. Calculated for C15H17F6NO2S: 389.4

Sources & evidence

ORD record: ord-4f9285e4d9f04bc8bb7d9354ad75eded
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296734B2

Reaction notes

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