Acetic Acid → [4-chloro-2-[4-(phenylsulfonyl)-1-piperazinylmethyl]phenoxy]-acetic Acid

HRID 38256Notes

Reaction equation

HRID 38256 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[C:4]([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:3]=1.[S:22](Cl)(Cl)(=[O:24])=[O:23].[OH-].[Na+].[C:29](O)(=O)[CH3:30]>C1COCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([S:22]([C:30]3[CH:29]=[CH:4][CH:3]=[CH:2][CH:14]=3)(=[O:24])=[O:23])[CH2:20][CH2:21]2)[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 86631054[4-chloro-2-(1-piperazinylmethyl)phenoxy]-acetic Acid, Ethyl Ester

Product 1

HCID 53317503[4-chloro-2-[4-(phenylsulfonyl)-1-piperazinylmethyl]phenoxy]-acetic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

The product of example 11 part b (300 mg) was dissolved in THF (10 ml) and triethylamine (0.28 ml). The sulfonyl chloride (1.1 equivalents) was added and stirred for 3 h. 1M NaOH (3 ml) was added and stirred for 2 hours. Acetic acid (5 ml) was added and then the reaction mixture was concentrated in vacuo. The residue was further purified by RPHPLC to give the sub-title compound (0.19 g).

Workup

  1. stirringstirred for 2 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was further purified by RPHPLC

Sources & evidence

ORD record
ord-5690df7e4f7f479abd9a68ea786d760c
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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