L-Alanine → (2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](Cl)=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:13][C@H:14]([C:16]([OH:18])=[O:17])[CH3:15].[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:13][C@H:14]([C:16]([OH:18])=[O:17])[CH3:15])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3,5-Difluorophenylacetyl chloride was added dropwise to a 0° C. solution of L-alanine (Aldrich) (16.7 g, 0.187 mol) in 2 N sodium hydroxide (215 mL, 0.43 mol). The reaction was stirred for 1 h at 0° C. and then overnight at room temperature. The reaction was diluted with water (100 mL), then extracted with ethyl acetate (3×150 mL). The organic layer was then washed with brine (200 mL), dried over MgSO4, and rotoevaporated at reduced pressure to a residue. Recrystallization of the residue from ethyl acetate/hexanes afforded the desired product (34.5 g, 82% yield).
Workup
- customovernight
- customat room temperature
- extractionextracted with ethyl acetate (3×150 mL)
- washThe organic layer was then washed with brine (200 mL)
- dry with materialdried over MgSO4
- customRecrystallization of the residue from ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-ba053bb2e84647f8881d07940e0af915
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486350B1
Reaction notes
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