HCID 21963939, compound → HCID 21963903, compound

HRID 2212366Notes

Reaction equation

HRID 2212366 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][C:23](=[O:25])[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:34][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:12][CH2:13][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][C:23]([CH3:34])([OH:25])[CH2:22]3)(=[O:19])=[O:20])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21963939HCID 21963939, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21963903HCID 21963903, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-[4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexylmethanesulfonyl]-azetidin-3-one (Example 31) (58 mg, 0.11 mmol.) in tetrahydrofuran (5 mL) was added a solution of methyl magnesium bromide (3M in diethyl ether, 0.075 mL, 0.22 mmol.) and the mixture stirred at ambient temperature for 45 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride (10 mL) and the mixture extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica, eluting with ethyl acetate:dichloromethane:iso-hexane (1:1:1), to afford the desired product (51 mg).

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride (10 mL)
  2. extractionthe mixture extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic layers were washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave a residue which
  7. customwas purified by column chromatography on silica
  8. washeluting with ethyl acetate:dichloromethane:iso-hexane (1:1:1)

Sources & evidence

ORD record
ord-8550ee333e6f4a7399f7d35d68680082
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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