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

HRID 2121853Notes

Reaction equation

HRID 2121853 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]

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 702EthanolSolvent

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-dc80ba46f1a94b7dbc21a04ba51adaa6
Source dataset
uspto-grants-2004_02
Patent number
US06696489B1

Reaction notes

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