Sodium Hydroxide → HCID 10478768, compound

HRID 1494079Notes

Reaction equation

HRID 1494079 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 (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-6df9f1da8c1c44e881a3c1c78e808b0f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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