Hydrochloric Acid → HCID 58277436, compound

HRID 1949279Notes

Reaction equation

HRID 1949279 reaction equation
O.[OH-].[Li+].[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=3)[N:16]=[C:15]([C:26]([O:28]CC)=[O:27])[CH:14]=2)[CH:9]=[C:10]([F:12])[CH:11]=1)#[N:5].Cl>C1COCC1>[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=3)[N:16]=[C:15]([C:26]([OH:28])=[O:27])[CH:14]=2)[CH:9]=[C:10]([F:12])[CH:11]=1)#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58277307HCID 58277307, compound

Product 1

HCID 58277436HCID 58277436, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.0 ml of water and 797 mg of lithium hydroxide (33.3 mmol) are added to 1.20 g (3.00 mmol) of the carboxylic ester of Example 134A with 90% purity in 45.0 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). 821 mg (82% 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-87ebe684f6154f2ebf6ed5ee9b279133
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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