Sodium Carbonate → Methyl {[2-(4-chlorophenyl)-2-oxoethyl]amino}acetate
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:17]>C(C(C)=O)C(C)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH2:15][NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[CH:19][CH:20]=1Participants
Procedure
A solution of glycine methyl ester hydrochloride (5.00 g, 39.8 mmol) in 80 ml methyl isobutyl ketone is treated with 12.6 g of sodium carbonate and the mixture stirred overnight at RT. Next, a solution of 2-bromo-1-(4-chlorophenyl)ethanone (8.37 g, 35.8 mmol) in 40 ml methyl isobutyl ketone is added dropwise to this suspension. The mixture is stirred for 1 hr more at RT, then the solid is suction-filtered and washed with 55 ml methyl isobutyl ketone. The filtrate is acidified with 12 ml of 6 N hydrochloric acid, then treated with 6.4 ml isopropanol. The precipitated solid is filtered off at the pump, washed with a little methyl isobutyl ketone, then stirred in 240 ml of acetonitrile and again suction-filtered. 3.41 g (34% of theory) of the pure title compound are thus obtained.
Workup
- stirringThe mixture is stirred for 1 hr more at RT
- filtrationthe solid is suction-filtered
- washwashed with 55 ml methyl isobutyl ketone
- additiontreated with 6.4 ml isopropanol
- filtrationThe precipitated solid is filtered off at the pump
- washwashed with a little methyl isobutyl ketone
- stirringstirred in 240 ml of acetonitrile
- filtrationagain suction-filtered
Sources & evidence
- ORD record
- ord-91eeafa3a24843b2b0303c7e42a06d5a
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084481B2
Reaction notes
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