Hydrochloric Acid → 8-(4-Chloro-benzenesulfonylamino)-4-(2-imidazol-1-yl-ethyl)-octanoic acid

HRID 1494100Notes

Reaction equation

HRID 1494100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10094868Methyl 8-(p-chlorophenylsulfonamido)-4-[2-(1-imidazolyl)ethyl]-octanoate

Product 1

HCID 100255698-(4-Chloro-benzenesulfonylamino)-4-(2-imidazol-1-yl-ethyl)-octanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.117 g of methyl 8-(p-chlorophenylsul- fonamido)-4-[2-(1-imidazolyl)ethyl]-octanoate in 3 mL methanol is mixed with 0.55 mL 1N sodium hydroxide. The mixture is heated at 50° for 4 hours. The reaction mixture is neutralized with 0.55 mL 1N hydrochloric acid and the solvent is evaporated. The residue is triturated with methylene chloride and the organic layer evaporated to dryness. The yellow oil is triturated with ether to obtain 8-(p-chlorophenylsulfonamido)-4-[2-(1-imidazolyl)ethyl]-octanoic acid as a crystalline solid, NMR (CDCl3): delta 7.82 (d,2H), 7.45 (d,2H), 4.15 (m,2H), 2.35 (t,2H).

Workup

  1. temperatureThe mixture is heated at 50° for 4 hours
  2. customthe solvent is evaporated
  3. customThe residue is triturated with methylene chloride
  4. customthe organic layer evaporated to dryness
  5. customThe yellow oil is triturated with ether

Sources & evidence

ORD record
ord-ffab3a03c40143f8bc2d89bf62f2af0f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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