Sodium Hydroxide → 2-[4-[2-(2-Benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid

HRID 1602511Notes

Reaction equation

HRID 1602511 reaction equation
[OH-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]=[CH:13][C:14]1[CH:48]=[CH:47][C:17]([C:18]([NH:20][C:21]2[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][S:37]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:31]=[CH:30][C:22]=2[O:23][CH2:24][C:25]([O:27]CC)=[O:26])=[O:19])=[CH:16][CH:15]=1>O1CCCC1>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]=[CH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:20][C:21]2[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][S:37]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:31]=[CH:30][C:22]=2[O:23][CH2:24][C:25]([OH:27])=[O:26])=[O:19])=[CH:47][CH:48]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54508018HCID 54508018, compound

Product 1

HCID 540226362-[4-[2-(2-Benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10% Sodium hydroxide aqueous solution (6 ml) was added at room temperature to a mixture of ethyl 2-[4-[2-(2-benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (196 mg, 0.29 mmol) and tetrahydrofuran (10 ml), and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, water was added the resulting residue, and then the solution was adjusted to pH 1 by adding concentrated hydrochloric acid. Thereafter, the solid material formed was collected by filtration, washed with water and ether in that order, dried under reduced pressure and then recrystallized from ethanol (50 ml) to give 2-[4-[2-(2-benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid (156 mg, 0.24 mmol, 83%) as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas added the resulting residue
  3. additionby adding concentrated hydrochloric acid
  4. customThereafter, the solid material formed
  5. filtrationwas collected by filtration
  6. washwashed with water and ether in that order
  7. customdried under reduced pressure
  8. customrecrystallized from ethanol (50 ml)

Sources & evidence

ORD record
ord-0f356b187faf4692861c8b567ce6de0a
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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