Sodium Acetate → (+)-(1R)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethanol

HRID 732116Notes

Reaction equation

HRID 732116 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[N:15][O:16][C:17](=O)[C@H:18]([OH:20])[CH3:19])[NH2:14])[CH:10]=[CH:11][CH:12]=1>O.C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:17]([C@H:18]([OH:20])[CH3:19])[O:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 866020063-chloro-N'-{[(2R)-2-hydroxypropanoyl]oxy}benzenecarboximidamide

Product 1

HCID 57838008(+)-(1R)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1.53 g (18.6 mmol) sodium acetate in water (12 mL) was added to 3.88 g (16.0 mmol) 3-chloro-N′-{[(2R)-2-hydroxypropanoyl]oxy}benzenecarboximidamide dissolved in ethanol (50 mL). The mixture was heated to 90° C. for 5.5 h and then evaporated to dryness and purified via flash chromatography (Hep/EA=9/1) to give after drying 2.3 g (65%) of the title compound. 1H NMR: 8.09 (t, 1 H), 7.97 (td, 1 H), 7.45-7.51 (m, 1 H), 7.42 (t, 1 H), 5.15 (qd, 1 H), 2.57 (d, 1 H), 1.72 (d, 3 H)

Workup

  1. customevaporated to dryness
  2. custompurified via flash chromatography (Hep/EA=9/1)
  3. customto give
  4. dry with materialafter drying 2.3 g (65%) of the title compound

Sources & evidence

ORD record
ord-54ccaeb453fa4f9d99c21fb0f42a921b
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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