Hydrochloric Acid → 4-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-butyric acid

HRID 2075737Notes

Reaction equation

HRID 2075737 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:14][C:15]3[N:16]2[CH:19]=[N:20][N:21]=3)=[CH:11][CH:10]=1)C.[Li+].[OH-].C1COCC1.Cl>O.CO>[C:22]1([C:13]2[C:12]3[C:17](=[CH:18][C:9]([S:8][CH2:7][CH2:6][CH2:5][C:4]([OH:28])=[O:3])=[CH:10][CH:11]=3)[N:16]3[CH:19]=[N:20][N:21]=[C:15]3[CH:14]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 670910824-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-butyric acid ethyl ester

Product 1

HCID 670909784-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-butyric acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

11d (40 mg, 0.10 mmol) was treated with 1N aqueous LiOH (2 mL) in 3:3:1 THF:MeOH:H2O (2 mL) overnight at room temperature. 1N aqueous HCl was added to adjust to pH 4, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the desired product, 11e.

Workup

  1. customat room temperature
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3f368766620f4a5fa7a902809ecee6dc
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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