Ammonium Chloride → HCID 86711998, compound

HRID 1051357Notes

Reaction equation

HRID 1051357 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])/[CH:5]=[N:6]/[S@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8].[CH2:18]([Mg]Br)[CH3:19].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C@H:5]([NH:6][S@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH2:18][CH3:19])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 89998981HCID 89998981, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86711998HCID 86711998, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 66 (3.0 g, 12 mmol) in THF (30 mL) at −78° C. was added a solution of ethylmagnesium bromide in THF (1N, 18 mL, 18 mmol). After stirring for 4 h, the reaction mixture was warmed to 25° C. and stirred at RT overnight. The mixture was treated with NH4Cl, and diluted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (1:1) to afford 1.5 g (45%) of (S)—N—((R)-1-(3-fluoro-4-methoxyphenyl)propyl)-2-methylpropane-2-sulfinamide (68). LCMS (ESI) m/z: 288.1 [M+H]+.

Workup

  1. stirringstirred at RT overnight
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by SiO2 chromatography
  6. washeluting with EtOAc/petroleum ether (1:1)

Sources & evidence

ORD record
ord-85f202ab078440b987e6314b8fdb1c20
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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