Hydrochloric Acid → HCID 58277353, compound

HRID 1949277Notes

Reaction equation

HRID 1949277 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:6]=[C:7]([N:11]2[C:15]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([C:23]#[N:24])[CH:17]=3)=[CH:14][C:13]([C:25]([O:27]CC)=[O:26])=[N:12]2)[CH:8]=[CH:9][CH:10]=1.Cl>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([N:11]2[C:15]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([C:23]#[N:24])[CH:17]=3)=[CH:14][C:13]([C:25]([OH:27])=[O:26])=[N:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58277301HCID 58277301, compound

Product 1

HCID 58277353HCID 58277353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.0 ml of water and 453 mg (18.9 mmol) of lithium hydroxide are added to 700 mg (1.89 mmol) of the carboxylic ester of Example 130A in 60.0 ml of THF. The mixture is stirred at RT overnight and a 1N aqueous hydrogen chloride solution is subsequently added to the reaction solution. The mixture is extracted with dichloromethane, and the combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). 712 mg (89% of theory) of the title compound are obtained in 81% purity.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. dry with materialthe combined organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-49147396e32c4f8cad4edff09ad63540
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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