Sodium Hydroxide → Arbaclofen

HRID 2068161Notes

Reaction equation

HRID 2068161 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH2:5][C:6]([OH:8])=[O:7].[OH-].[Na+]>O>[NH2:2][CH2:3][C@@H:4]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44601Arbaclofen Hydrochloride

Product 1

HCID 44602ArbaclofenYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, (R)-4-amino-3-(4-chlorophenyl)butanoic acid hydrochloride (4.0 g, 16.0 mmol) was dissolved in water (12 ml). Into this, 1 mol/L sodium hydroxide aqueous solution was dropped, to adjust pH to 6.5. The crystallized crystal was filtrated and dried under reduced pressure to obtain a title compound (3.13 g, 14.6 mmol) (yield: 91%). The optical purity of the resultant title compound was measured by HPLC to find a value of 99.9% ee or more (conditions are shown below).

Workup

  1. filtrationThe crystallized crystal was filtrated
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-aa388a40c61946dda2ed31a73f00c3ec
Source dataset
uspto-grants-2012_10
Patent number
US08293926B2

Reaction notes

Loading…