Potassium Hydroxide → HCID 178516894, compound

HRID 2261878Notes

Reaction equation

HRID 2261878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[C:15](=[O:26])[C:16]4[C:21]([C:22](=[O:25])[C:23]=3Cl)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:27].[K+]>CO.O>[CH:18]1[CH:19]=[CH:20][C:21]2[C:22]([C:23]([OH:27])=[C:14]([C@@H:11]3[CH2:10][CH2:9][C@@H:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)[C:15](=[O:26])[C:16]=2[CH:17]=1)=[O:25]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178516332HCID 178516332, compound

Product 1

HCID 178516894HCID 178516894, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
31 °C

Procedure

The residue obtained (Formula IV) was suspended in 4.5 liter methanol. A solution of potassium hydroxide (225 gm) in water (1550 ml) was added drop-wise under heating over a period of one hour. The reaction mass was then refluxed for 2 hours and cooled to 30-32° C. and filtered. The filtrate was neutralized with 50% aqueous hydrochloric acid to precipitate atovaquone in a cis/trans-isomeric mixture (116 gm).

Workup

  1. temperatureunder heating over a period of one hour
  2. temperatureThe reaction mass was then refluxed for 2 hours
  3. filtrationfiltered
  4. customto precipitate atovaquone in a cis/trans-isomeric mixture (116 gm)

Sources & evidence

ORD record
ord-5e57d63cd0ae4551899c5d5e49f42775
Source dataset
uspto-grants-2010_12
Patent number
US07847127B2

Reaction notes

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