Hydrochloric Acid → HCID 57600004, compound

HRID 1787460Notes

Reaction equation

HRID 1787460 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([C:11]2[CH:16]=[C:15]([C:17](=[O:36])[NH:18][C:19]3[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[C:21]([S:29](=[O:33])(=[O:32])[NH:30][CH3:31])[C:20]=3[O:34][CH3:35])[CH:14]=[CH:13][C:12]=2[CH3:37])[CH:10]=1)=[O:5])C.[Li+].[OH-].Cl>CO.O>[C:25]([C:23]1[CH:22]=[C:21]([S:29](=[O:33])(=[O:32])[NH:30][CH3:31])[C:20]([O:34][CH3:35])=[C:19]([NH:18][C:17]([C:15]2[CH:14]=[CH:13][C:12]([CH3:37])=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[N:8]3)[CH:16]=2)=[O:36])[CH:24]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57599992HCID 57599992, compound

Product 1

HCID 57600004HCID 57600004, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The above ester (230 mg, 0.434 mmol) was dissolved in 7 mL of MeOH. A solution of 250 mg (5.99 mmol) of LiOH in 2 mL of water was added at RT. The resulting mixture was stirred overnight, then acidified with 4N HCl and extracted with EtOAc (4×30 mL). The extracts were combined, dried over MgSO4, filtered and concentrated to provide 223 mg of 1-[5-(5-tert-Butyl-2-methoxy-3-methylsulfamoyl-phenylcarbamoyl)-2-methyl-phenyl]-1H-[1,2,3]triazole-4-carboxylic acid as a brown foam (>90% by LCMS).

Workup

  1. extractionextracted with EtOAc (4×30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67dfc78af1bc4a9eb0fd77aa925124e1
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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