Hydrochloric Acid → HCID 58277275, compound

HRID 1949278Notes

Reaction equation

HRID 1949278 reaction equation
O.[OH-].[Li+].[C:4]([C:6]1[CH:7]=[C:8]([N:13]2[C:17]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([C:25]#[N:26])[CH:19]=3)=[CH:16][C:15]([C:27]([O:29]CC)=[O:28])=[N:14]2)[CH:9]=[CH:10][C:11]=1[F:12])#[N:5].Cl>C1COCC1>[C:4]([C:6]1[CH:7]=[C:8]([N:13]2[C:17]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([C:25]#[N:26])[CH:19]=3)=[CH:16][C:15]([C:27]([OH:29])=[O:28])=[N:14]2)[CH:9]=[CH:10][C:11]=1[F:12])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58277422HCID 58277422, compound

Product 1

HCID 58277275HCID 58277275, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 ml of water and 570 mg (23.8 mmol) of lithium hydroxide are added to 900 mg (1.78 mmol) of the carboxylic ester of Example 132A with 75% purity in 30.0 ml of THF. The mixture is stirred at RT for 5 h 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). 527 mg (86% of theory) of the title compound are obtained.

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-f245bddfbd064f27b3cd25bc55e38f05
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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