Lithium Hydroxide → HCID 58011944, compound

HRID 660952Notes

Reaction equation

HRID 660952 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([O:16]CC)=[O:15])[C:11](=[O:19])[N:10]([CH2:20][C:21]([NH:23][C:24]([CH3:36])([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[CH3:25])=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([OH:16])=[O:15])[C:11](=[O:19])[N:10]([CH2:20][C:21]([NH:23][C:24]([CH3:36])([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=3)[CH3:25])=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58012188HCID 58012188, compound

Product 1

HCID 58011944HCID 58011944, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

237 mg (0.45 mmol) of ethyl {3-(4-chlorophenyl)-1-[2-({1-methyl-1-[3-(trifluoromethyl)phenyl]-ethyl}amino)-2-oxoethyl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl}-acetate from Example 429 are dissolved in 3 ml of methanol and treated with 0.9 ml of 1 N aqueous lithium hydroxide solution. This is stirred for 24 hrs at RT. The reaction mixture is then concentrated under reduced pressure. 5 ml of water are added, and the mixture is acidified with 1 ml of 1 N hydrochloric acid and extracted twice with 10 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. The product that remains is freed from solvent residues under high vacuum. 220 mg (97% of theory) of the target compound are thus obtained.

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. addition5 ml of water are added
  3. extractionextracted twice with 10 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custom220 mg (97% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-16e87ee430214e6fabcaf3fa48c12580
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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