Hydrochloric Acid → HCID 66919893, compound

HRID 1971670Notes

Reaction equation

HRID 1971670 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:36])[C:18]([N:20]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:21][CH2:22][S:23][CH2:24][C:25]#[C:26][C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[O:19])[CH:9]2[C:12]([O:14]CC)=[O:13])=[CH:4][C:3]=1[O:37][CH3:38].[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:36])[C:18]([N:20]([C:32]([CH3:34])([CH3:35])[CH3:33])[CH2:21][CH2:22][S:23][CH2:24][C:25]#[C:26][C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[O:19])[CH:9]2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:37][CH3:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66919832HCID 66919832, compound

Product 1

HCID 66919893HCID 66919893, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 505 mg of 9h in 6 ml of dioxane and a solution of 180 mg of KOH in 1 ml of water were mixed and stirred for 3 h at 50° C. The reaction mixture was cooled and diluted with 20 ml of water and acidified to pH 3 by addition of 0.5 N HCl and extracted with ethyl acetate. The extract was once washed with water, dried and concentrated, to provide 480 mg of crude and unstable 91, which was used without further purification directly in the next step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was once washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto provide 480 mg of crude and unstable 91, which
  7. customwas used without further purification directly in the next step

Sources & evidence

ORD record
ord-2ced6e9b394446a7b851d7d6f588f8a0
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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