Methyl (2RS,3SR)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionate → (2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionic acid

HRID 1533250Notes

Reaction equation

HRID 1533250 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH:16]([CH:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[OH:22])[C:17]([O:19]C)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[K+]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH:16]([CH:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[OH:22])[C:17]([OH:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86756554Methyl (2RS,3SR)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionate

Product 1

HCID 22012301(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Methyl (2RS,3SR)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionate (1.14 g) was dissolved in a methanolic 1M solution of potassium hydroxide (11 ml) and the mixture was heated under reflux for 4 hours. The solution was concentrated in vacuo and the residue was dissolved in water and washed with diethyl ether. The aqueous layer was acidified by aqueous 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried and evaporated under reduced pressure to give (2RS,3SR)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionic acid (0.998 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in water
  5. washwashed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-36cc4a62e09a4d73811c9136ab07fc17
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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