(NE,R)-N-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methylidene]-2-methylpropane-2-sulfinamide → (R)-N-((S)-1-(5-(4-chlorophenyl)isoxazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide

HRID 57417Notes

Reaction equation

HRID 57417 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13](/[CH:16]=[N:17]/[S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH:12]=2)=[CH:7][CH:6]=1>C(Cl)Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C@@H:16]([NH:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH3:1])[CH:12]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 90415066(NE,R)-N-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methylidene]-2-methylpropane-2-sulfinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 90416188(R)-N-((S)-1-(5-(4-chlorophenyl)isoxazol-3-yl)ethyl)-2-methylpropane-2-sulfinamideYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methylmagnesium bromide (3.0 M in diethyl ether, 12.8 mL, 38.4 mmol, 4 equiv) was added to a solution of (R,E)-N-((5-(4-chlorophenyl)isoxazol-3-yl)methylene)-2-methylpropane-2-sulfinamide (2.98 g, 9.6 mmol) in DCM (96 mL) at 0° C. The solution became orange, then faded to yellow. The reaction was stirred at 0° C. for 30 min and then carefully quenched with saturated aqueous ammonium chloride (100 mL). The layers were separated and the aqueous layer was extracted with DCM (40 mL). The combined organic layers were washed with water (50 mL), saturated aqueous sodium chloride (50 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane) provided (R)—N—((S)-1-(5-(4-chlorophenyl)isoxazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide (1.0 g, white solid) in 32% yield. 1H NMR (400 MHz, CDCl3) δ 7.71 (d, J=8.6 Hz, 2H), 7.45 (d, J=8.6 Hz, 2H), 6.50 (s, 1H), 4.75 (m, 1H), 3.47 (m, 1H), 1.70 (d, J=6.8 Hz, 3H), 1.25 (s, 9H). MS m/z 327.0 (M+H)+; Rt-0.94 min.

Workup

  1. customcarefully quenched with saturated aqueous ammonium chloride (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (40 mL)
  4. washThe combined organic layers were washed with water (50 mL), saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f21620ca988442a95ce2dc96b6d7a39
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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