Water → HCID 178439710, compound

HRID 1165192Notes

Reaction equation

HRID 1165192 reaction equation
[C:1]([C:4]1[CH:35]=[CH:34][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[NH:17][N:16]=[C:15]([NH:18][C:19](=[O:33])[CH2:20][C:21]([O:23]CC3C=CC(OC)=CC=3)=[O:22])[N:14]=2)=[C:6]([CH2:36][CH2:37][CH3:38])[C:5]=1[OH:39])(=[O:3])[CH3:2].O>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[C:1]([C:4]1[CH:35]=[CH:34][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[NH:17][N:16]=[C:15]([NH:18][C:19](=[O:33])[CH2:20][C:21]([OH:23])=[O:22])[N:14]=2)=[C:6]([CH2:36][CH2:37][CH3:38])[C:5]=1[OH:39])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 178439709HCID 178439709, compound

Product 1

HCID 178439710HCID 178439710, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

In a mixture of 1.5 ml of trifluoroacetic acid and 0.1 ml of anisole was dissolved 100 mg of p-methoxybenzyl 3-[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1H-1,2,4-triazol-3-yl]amino]-3-oxopropionate obtained in Example 31 at 10° to 20° C. and after stirring the solution thus obtained for 30 minutes, trifluoroacetic acid was distilled off under reduced pressure. The residue thus formed was mixed with 20 ml of water and extracted with 20 ml of ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off to provide a solid product. The solid product was washed with methylene chloride and dried to provide 50 mg of 3-[[5-[[-3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1H-1,2,4-triazol-3-yl]amino]-3-oxopropionic acid.

Workup

  1. customthus obtained for 30 minutes
  2. distillationtrifluoroacetic acid was distilled off under reduced pressure
  3. customThe residue thus formed
  4. extractionextracted with 20 ml of ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customto provide a solid product
  9. washThe solid product was washed with methylene chloride
  10. customdried

Sources & evidence

ORD record
ord-653eb0c1a3244c95ad0a1e272d012733
Source dataset
uspto-grants-1990_03
Patent number
US04908368

Reaction notes

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