Sodium Hydroxide → HCID 9933468, compound

HRID 1872225Notes

Reaction equation

HRID 1872225 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:7]1([C:12](=[O:15])[NH:13][OH:14])[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+]>CO>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:21]=[CH:20][C:19]([S:16]([N:6]([C:7]3([C:12](=[O:15])[NH:13][OH:14])[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:5][CH2:4][C:3]([OH:32])=[O:2])(=[O:17])=[O:18])=[CH:24][CH:23]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9804476HCID 9804476, compound

Product 1

HCID 9933468HCID 9933468, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[(4'-fluorobiphenyl-4-sulfonyl)-(1-hydroxycarbamoylcyclopentyl)amino]-propionic acid methyl ester (8.9 grams, 19.2 mmole) in methanol (500 mL) was treated with aqueous 1 N sodium hydroxide solution (95 mL, 95 mmole) and stirred at room temperature for 5.5 hours. The mixture was concentrated to remove methanol, diluted with water, acidified with 6 N aqueous hydrochloric acid solution and extracted with ethyl acetate. After washing with water and brine the organic extract was dried over magnesium sulfate and concentrated to afford 3-[(4'-fluorobiphenyl-4-sulfonyl)-(1-hydroxycarbamoyl-cyclopentyl)amino]propionic acid as a white foam which was crystallized from ethyl acetate (6.74 grams, 78%).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove methanol
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washAfter washing with water and brine the
  6. extractionorganic extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2995f1e4cb9d46598199f3ed8760ddf4
Source dataset
uspto-grants-2000_08
Patent number
US06107337

Reaction notes

Loading…