Sodium Hydroxide → 3-[2-((1R)-1-{(2R)-2-Hydroxy-3-[2-methyl-1-(naphthalen-2-yl)propan-2-ylamino]propoxy}ethyl)phenyl]propionic acid

HRID 1181589Notes

Reaction equation

HRID 1181589 reaction equation
[OH:1][C@H:2]([CH2:19][NH:20][C:21]([CH3:34])([CH3:33])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:3][O:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[CH3:6].[OH-].[Na+]>CO.O1CCCC1>[OH:1][C@H:2]([CH2:19][NH:20][C:21]([CH3:33])([CH3:34])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:3][O:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH3:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58662623Methyl 3-[2-[(1R)-1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]propionate

Product 1

HCID 114083023-[2-((1R)-1-{(2R)-2-Hydroxy-3-[2-methyl-1-(naphthalen-2-yl)propan-2-ylamino]propoxy}ethyl)phenyl]propionic acidYield 63.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 3-[2-[(1R)-1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]propionate (539 mg) obtained in Step 4 was dissolved in methanol (20 ml) and tetrahydrofuran (20 ml), 4N aqueous sodium hydroxide (2.5 ml) was added and the mixture was stirred at 50° C. for 8 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with water, neutralized with 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (332 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef6553b2106d463ea01c943acc48eaf1
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

Loading…