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

HRID 465556Notes

Reaction equation

HRID 465556 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-chlorophenylsulfonamido)-4-[2-(1-imidazolyl)ethyl]-octanoate in 3 ml methanol is mixed with 0.55 ml 1N aqueous sodium hydroxide. The mixture is heated at 50° for 4 h. 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 h
  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-2c3ff6ff2bd04745974d882b49cb7b11
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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