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Hydrochloric Acid → 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acid

HRID 1862630
Notes
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Reaction equation

HRID 1862630 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][NH:17][C@@H:18]([CH3:28])[C@H:19]([OH:27])[C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][NH:17][C@@H:18]([CH3:28])[C@H:19]([OH:27])[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15895329ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate

Product 1

HCID 115536082-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acidYield 28.7%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a solution of ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate (327 mg) in ethanol (3.3 ml) was added 1N aqueous sodium hydroxide solution (1.45 ml), and the mixture was stirred for 15 hours at room temperature. 1N Hydrochloric acid (1.45 ml) was added to the stirred reaction mixture under ice-cooling, and the solvent was removed under reduced pressure. To the residue was added water, and the resulting insoluble material was collected by filtration to give 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acid (88 mg).

Workup

  1. temperaturecooling
  2. customthe solvent was removed under reduced pressure
  3. additionTo the residue was added water
  4. filtrationthe resulting insoluble material was collected by filtration

Sources & evidence

ORD record
ord-ee435a088b224a548aa7b4aac5a0e8cb
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06538152B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes