Hydrochloric Acid → N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-aminoacetic acid

HRID 275999Notes

Reaction equation

HRID 275999 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH:10][C@@H:11]([CH3:21])[C@H:12]([OH:20])[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:5]=[C:4]([Cl:22])[C:3]=1[NH:23][CH2:24][C:25]([O:27]CC)=[O:26].Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH:10][C@@H:11]([CH3:21])[C@H:12]([OH:20])[C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[CH:5]=[C:4]([Cl:22])[C:3]=1[NH:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10717980HCID 10717980, compound

Product 1

HCID 9844606N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-aminoacetic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]aminoacetate (500 mg) was dissolved in 1N aqueous sodium hydroxide solution (5.0 ml), and the solution was stirred for 1 hour at room temperature. To the reaction mixture was added 1N hydrochloric acid (5.0 ml) under ice-cooling with stirring, and collection of the resulting precipitates by filtration gave N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-aminoacetic acid (464 mg).

Workup

  1. temperaturecooling
  2. stirringwith stirring
  3. customcollection of the resulting
  4. customprecipitates by filtration

Sources & evidence

ORD record
ord-c3505e1b015845eca2c7764d18b84036
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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