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Hydrochloric Acid → 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]-2-methylpropionic acid

HRID 1006461
Notes
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Reaction equation

HRID 1006461 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[CH2:17][CH2:18][NH:19][C@@H:20]([CH3:30])[C@H:21]([OH:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[O:5][C:6]([CH3:13])([CH3:12])[C:7]([O:9]CC)=[O:8].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[CH2:17][CH2:18][NH:19][C@@H:20]([CH3:30])[C@H:21]([OH:29])[C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)[O:5][C:6]([CH3:12])([CH3:13])[C:7]([OH:9])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12096594ethyl 2-[3-Chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]-2-methylpropionate

Product 1

HCID 698830302-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]-2-methylpropionic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a solution of ethyl 2-[3-Chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]-2-methylpropionate (2.39 g) in ethanol (20 ml) was added 2N aqueous sodium hydroxide solution (8.2 ml ), and the mixture was stirred for 13 hours at room temperature. To the stirred reaction mixture was added 2N hydrochloric acid (8.2 ml) under ice-cooling. After the reaction mixture was concentrated under reduced pressure, azeotropic concentration with ethanol was undergone. The residue was washed with water (180 ml) and dried under reduced pressure to give 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]-2-methylpropionic acid (2.02 g).

Workup

  1. customTo the stirred reaction mixture
  2. temperaturecooling
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, azeotropic concentration with ethanol
  4. washThe residue was washed with water (180 ml)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-954b37d9237d4a7dbd1ce9d352658d40
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06790865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes