Sodium Hydroxide → (2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy) acetic acid

HRID 1108772Notes

Reaction equation

HRID 1108772 reaction equation
ClC1C=C([C@@H](O)CNC2CCCC(C3C=CC=CC=3OCC([O-])=O)C2)C=CC=1.[Na+].[Cl:30][C:31]1[CH:32]=[C:33]([C@@H:37]([OH:59])[CH2:38][NH:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH:42]([C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([O:52][CH2:53][C:54]([O:56]CC)=[O:55])[CH:47]=3)[CH2:41]2)[CH:34]=[CH:35][CH:36]=1.[OH-].[Na+]>C(O)C>[Cl:30][C:31]1[CH:32]=[C:33]([C@@H:37]([OH:59])[CH2:38][NH:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH:42]([C:46]3[CH:47]=[C:48]([CH:49]=[CH:50][CH:51]=3)[O:52][CH2:53][C:54]([OH:56])=[O:55])[CH2:41]2)[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 9912456(1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl)cyclohexylamino]ethanolHCID 131721829Sodium (2R)-(2-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy)acetate

Product 1

HCID 11165592(2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy) acetic acidYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the trans-H compound, (1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl)cyclohexylamino]ethanol (hydrochloride), obtained in Example 11 (220 mg) in ethanol (10 ml) there was added 1 N sodium hydroxide solution (2.5 ml), and the mixture was stirred at room temperature for 2 hours. After concentrating the reaction solution under reduced pressure, water (2 ml) was added, and after adding 1 N aqueous solution of hydrochloric acid (2.03 ml) while stirring and cooling on ice, the deposited crystals were filtered off and dried to give 153 mg of (2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy) acetic acid (trans-H) as a white crystalline powder (81% yield).

Workup

  1. concentrationAfter concentrating the reaction solution under reduced pressure, water (2 ml)
  2. additionwas added
  3. additionafter adding 1 N aqueous solution of hydrochloric acid (2.03 ml)
  4. stirringwhile stirring
  5. temperaturecooling on ice
  6. filtrationthe deposited crystals were filtered off
  7. customdried

Sources & evidence

ORD record
ord-9e8fd3e1e7f846498bc048b539314745
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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