HCID 58762402, compound → HCID 15271313, compound

HRID 1453019Notes

Reaction equation

HRID 1453019 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1S[C:14](=[O:25])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>C1COCC1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][C:14](=[O:25])[CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 58762402HCID 58762402, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 15271313HCID 15271313, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Isobutylmagnesium bromide (0.88 mL, 1.75 mmol, 2M soln in THF) was added to a cooled −78° C. solution of 3-(4-Methoxy-phenyl)-thiopropionic acid S-pyridin-2-yl ester (0.4 g, 1.46 mmol, from Step 1) dissolved in THF (6 mL). The reaction mixture was stirred for 60 min. The reaction was quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to a yellow oil. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the title compound as a clear oil (0.24 g, 75%). 1H NMR (CDCl3): δ 0.89 (d, 6H, J=6.6 Hz), 2.12 (m, 1H), 2.26 (d, 2H, J=7.0 Hz), 2.60-2.69 (m, 2H), 2.81-2.90 (m, 2H), 3.78 (s, 3H), 6.82 (d, 2H, J=8.7 Hz), 7.09 (d, 2H, J=8.7 Hz).

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a yellow oil
  6. customThe residue was purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-838335113fcf41a49e5f6e9d4352d20b
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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