Hydrochloric Acid → HCID 86732257, compound

HRID 930418Notes

Reaction equation

HRID 930418 reaction equation
CN(C)/N=[C:4](\[C:24]([F:27])([F:26])[F:25])/[CH2:5][C:6]([NH:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[F:16])[CH2:7][F:8].Cl.C([O:32]CC)C>O.O1CCOCC1>[CH3:21][C:20]([S@:18]([NH:17][C@:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[F:16])([CH2:5][C:4](=[O:32])[C:24]([F:27])([F:26])[F:25])[CH2:7][F:8])=[O:19])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90373274HCID 90373274, compound

Product 1

HCID 86732257HCID 86732257, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (R)-N-((Z)-4-(2,2-dimethylhydrazono)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)pentan-2-yl)-2-methylpropane-2-sulfinamide (5.66 g, 13.24 mmol) in 10% water (5 mL) in dioxane (50 mL) was added hydrogen chloride, 1m in diethyl ether (26.5 ml, 26.5 mmol) and the resulting mixture was stirred at 40° C. for 1 h. The reaction was quenched with water, diluted with EtOAc and washed with water. The organic phase was dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-40% EtOAc/hexanes to afford a yellow oil as (R)-2-methyl-N-((S)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)-4-oxopentan-2-yl)propane-2-sulfinamide (3.80 g, 75% yield). MS m/z=385.9 [M+H]+. Calculated for C16H20F5NO2S: 385.11.

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel using 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-c26c9fb8b8c94dd2994e20397d6aad43
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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