Water → HCID 58011945, compound

HRID 660883Notes

Reaction equation

HRID 660883 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:7]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[O:26][CH3:27])=[N:6]1.[OH-].[Li+].O>CO>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:7]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:9](=[O:10])[N:5]([CH2:4][C:3]([OH:28])=[O:2])[N:6]=2)=[C:20]([O:26][CH3:27])[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58011821Methyl[3-(4-chloro-2-methoxyphenyl)-4-(3-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 58011945HCID 58011945, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

159 mg (0.39 mmol) of the compound from Example 147A in 4 ml methanol are treated with 1.57 ml of a 1 N solution of lithium hydroxide in water (1.57 mmol) and the resulting mixture is stirred overnight at RT. The methanol is removed on the rotary evaporator, the residue diluted with water and the resulting aqueous phase extracted twice with dichloromethane. These organic phases are discarded. The aqueous phase is then acidified with 1 N hydrochloric acid and extracted three times with dichloromethane. The extracts are combined, dried over magnesium sulphate, freed of solvent on the rotary evaporator and the residue dried under high vacuum. 144 mg (94% of theory) of the title compound are obtained.

Workup

  1. customThe methanol is removed on the rotary evaporator
  2. additionthe residue diluted with water
  3. extractionthe resulting aqueous phase extracted twice with dichloromethane
  4. extractionextracted three times with dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. customfreed of solvent on the rotary evaporator
  7. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-b8f0e975a5d7476398bfa3fa6c6f086d
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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