Sodium Hydroxide → HCID 10478768, compound

HRID 465536Notes

Reaction equation

HRID 465536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH:14]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH:14]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14986640HCID 14986640, compound

Product 1

HCID 10478768HCID 10478768, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 8-(p-chlorophenylsulfonamido)-6-(3-pyridylmethyl)-octanoate of example 11 (0.3 g) is dissolved in 10 ml of methanol, 20 ml of 1N aqueous NaOH added and the reaction is stirred at room temperature overnight. The methanol is evaporated off, water added and the mixture extracted with ethyl acetate. The aqueous layer is acidified to pH 6.1 and extracted with ethyl acetate. The ethyl acetate extract is dried over magnesium sulfate, filtered and concentrated to give 8-(p-chlorophenylsulfonamido)-6-(3-pyridylmethyl)-octanoic acid, NMR (CDCl3): delta 7.7 (d,2H), 7.4 (d,2H), 2.9 (m,2H).

Workup

  1. customThe methanol is evaporated off
  2. additionwater added
  3. extractionthe mixture extracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialis dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-31005de2d3944598962c798757e9370a
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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