HCID 67423230, compound → HCID 86609589, compound

HRID 1172222Notes

Reaction equation

HRID 1172222 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([CH3:23])[C:8]([C@@:10]2([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[CH2:12][C@H:11]2[CH2:13][OH:14])=[O:9])=[CH:4][CH:3]=1>CC(C)=O>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([CH3:23])[C:8]([C@@:10]2([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[CH2:12][C@H:11]2[CH:13]=[O:14])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67423230HCID 67423230, compound

Product 1

HCID 86609589HCID 86609589, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(1S,2R)-1-(3,4-Dichloro-phenyl)-2-hydroxymethyl-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide (4.60 g, 12.0 mmol) is dissolved in acetone (240 ml) and IBX (10.1 g, 36.1 mmol) is added (IBX concentration 0.15M). The mixture is heated to reflux for 2 hours, then cooled to ambient temperature. The solids are filtered off and the filtrate concentrated in vacuo. The crude product is eluted through a short silica gel column with ethyl acetate:heptane (50:50). 3.57 g (78%) of the product is obtained as a highly viscuous light yellow oil. LC/MS (m/z) 380.0 (M+H+).

Workup

  1. additionIBX (10.1 g, 36.1 mmol) is added (IBX concentration 0.15M)
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 2 hours
  4. filtrationThe solids are filtered off
  5. concentrationthe filtrate concentrated in vacuo
  6. washThe crude product is eluted through a short silica gel column with ethyl acetate:heptane (50:50)

Sources & evidence

ORD record
ord-497921f6d7be4426a07221ea98f44f89
Source dataset
uspto-grants-2010_11
Patent number
US07834008B2

Reaction notes

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