Chloroacetamide → 2-Aminocarbonylmethoxyimino-2-(fur-2-yl)acetic acid
Reaction equation
CC(C)([O-])C.[K+].[OH:7][N:8]=[C:9]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[C:10]([OH:12])=[O:11].Cl[CH2:19][C:20]([NH2:22])=[O:21]>CS(C)=O>[NH2:22][C:20]([CH2:19][O:7][N:8]=[C:9]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[C:10]([OH:12])=[O:11])=[O:21]Participants
Procedure
To a solution of potassium t-butoxide (2.24 g) in dimethylsulphoxide (10 ml) was added a solution of 2-hydroxyimino-2-(fur-2-yl)acetic acid (syn isomer) (1.551 g) in dimethylsulphoxide (10 ml). The mixture was stirred for 30 minutes and a solution of chloroacetamide (0.935 g) in dimethylsulphoxide (10 ml) was added. The mixture was stirred for a further 2 hours, when a clear solution had formed. This solution was poured into ice-water (50 ml) and the mixture was extracted with ethyl acetate. The layers were separated and the aqueous layer was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine and dried, and the solvent was evaporated. The resulting yellow oil was triturated with dichloromethane to give the title compound (0.51 g, 24%), m.p. 143°-145°; λ max (EtOH) 275nm (ε 14,100).
Workup
- stirringThe mixture was stirred for a further 2 hours
- customwhen a clear solution had formed
- extractionthe mixture was extracted with ethyl acetate
- customThe layers were separated
- extractionextracted with ethyl acetate
- washThe ethyl acetate extracts were washed with brine
- customdried
- customthe solvent was evaporated
- customThe resulting yellow oil was triturated with dichloromethane
Sources & evidence
- ORD record
- ord-b4d0e5d652434e85844b9c319e8c5fad
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04074047
Reaction notes
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