Hydrochloric Acid → HCID 66919870, compound

HRID 1971701Notes

Reaction equation

HRID 1971701 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:34])[C:18]([N:20]([CH3:33])[C:21]([CH3:32])([CH2:23][CH2:24][C:25]#[C:26][C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)[CH3:22])=[O:19])[CH:9]2[C:12]([O:14]CC)=[O:13])=[CH:4][C:3]=1[O:35][CH3:36].[OH-].[K+].Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:34])[C:18]([N:20]([CH3:33])[C:21]([CH3:22])([CH2:23][CH2:24][C:25]#[C:26][C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)[CH3:32])=[O:19])[CH:9]2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:35][CH3:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58124839HCID 58124839, compound

Product 1

HCID 66919870HCID 66919870, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 110 mg of 12i in 3 ml of dioxane a solution of 50 mg of KOH in 1 ml of water was added. The mixture was stirred at 50° C. for 2 hr. After cooling to RT, 15 ml of water was added and the reaction mixture was acidified to pH3 by addition of cold 0.5 N HCl. The product was extracted into ethyl acetate. The extract was once washed with water, dried and concentrated, to provide 100 mg of the acid 12j as colorless amorphous material, used without further purification in the next step; MS-ESI: [M+1] 546.98, 548.98).

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe product was extracted into ethyl acetate
  3. washThe extract was once washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd72de76d8d14f30b670378c838fce53
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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