1-Propanol → HCID 178459586, compound

HRID 221363Notes

Reaction equation

HRID 221363 reaction equation
S(Cl)(Cl)=O.[N:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C@H:16]3[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.[CH2:25](O)[CH2:26][CH3:27]>>[CH2:25]([O:23][C:22]([C@H:19]1[CH2:18][CH2:17][C@H:16]([C:14]2[O:13][N:12]=[C:11]([C:8]3[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=3)[N:15]=2)[CH2:21][CH2:20]1)=[O:24])[CH2:26][CH3:27]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 24386Thionyl ChlorideHCID 178525699HCID 178525699, compound

Product 1

HCID 178459586HCID 178459586, compound

Procedure

Thionyl chloride (11.5 μl, 0.1 mmol) was added to a solution of trans-4-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)cyclohexanecarboxylic acid (Preparation 4, 22 mg, 0.08 mmol) in 1-propanol (2 ml). The mixture was heated under reflux for 2 h, cooled and the solvent removed in vacuo. The residue was dissolved in EtOAc (10 ml), washed with saturated aqueous NaHCO3 (3 ml) and brine (5 ml), then dried (MgSO4). Removal of the solvent afforded the title compound. RT=3.67 min, m/z (ES+)=316.3 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (10 ml)
  6. washwashed with saturated aqueous NaHCO3 (3 ml) and brine (5 ml)
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-88f885a70f51427ba6f271d6bcfc33f5
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

Loading…