Propan-2-one--water (1/1) → HCID 22177238, compound

HRID 1797162Notes

Reaction equation

HRID 1797162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:29])[CH:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=3)=[CH:17][CH:16]=2)[CH2:12][CH:13]=C)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CC(C)=[O:32].O>O=[Os](=O)(=O)=O>[C:27]([C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([CH:11]([CH2:12][CH:13]=[O:32])[C:10]([NH:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)=[O:29])=[CH:16][CH:17]=2)[CH:26]=[CH:25][CH:24]=1)#[N:28]

Participants

4

Reactant 2

HCID 18366337Propan-2-one--water (1/1)HCID 86587977HCID 86587977, compound

Product 1

HCID 22177238HCID 22177238, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 2-(3′-cyano-biphenyl-4-yl)-pent-4-enoic acid (3,5-dichloro-phenyl)-amide (680 mg, 1.6 mmol) in 9 mL of acetone/H2O (2:1 v/v) was added OsO4 (4% in H2O, 100 L, 1 mmol %) and NaIO4 (860 mg, 4.0 mmol, 2.5 eq). The reaction mixture was stirred at r.t. for 6 h. The mixture was then partitioned between CH2Cl2 (20 mL) and 10% NaHCO3 (20 mL) and the organic layer separated. The aqueous layer was extracted with CH2Cl2 (10 mL×3) and the combined organic layer was washed with saturated brine (10 mL), dried (Na2SO4), and concentrated. Chromatography on silica gel (20% EtOAc/hexanes) gave 2-(3′-cyano-biphenyl-4-yl)-N-(3,5-dichloro-phenyl)-4-oxobutyramide as a light yellow oil (300 mg, 44%). MS(ESI): 423.0 (M+1).

Workup

  1. customThe mixture was then partitioned between CH2Cl2 (20 mL) and 10% NaHCO3 (20 mL)
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (10 mL×3)
  4. washthe combined organic layer was washed with saturated brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-75a9a787ad604fbe8cf58e701a4b14bf
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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