Water → HCID 178439710, compound

HRID 1646086Notes

Reaction equation

HRID 1646086 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-b35bd19ecb244bc5b77603318b57b987
Source dataset
uspto-grants-1993_01
Patent number
US05177215

Reaction notes

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