Glyoxylic Acid → 37662-06-9
Reaction equation
[CH3:1][C@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]1([CH3:16])C=CC=CC=1.[C:17]([OH:21])(=[O:20])[CH:18]=O>O>[C:3]1([C@@H:2]([N:9]=[CH:18][C:17]([O:21][CH2:10][CH3:16])=[O:20])[CH3:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
The synthesis was performed according to the procedure reported in the literature. (S)-(−)-α-Methylbenzylamine (238.6 g, 1.964 mol) was added into 2 L round bottom flask equipped a stirrer bar. Toluene (520 mL) was added. The reaction mixture was cooled to −5° C., and was allowed to stir for 10 min. Glyoxylic acid (200 g, 1.96 mol) was tranferred to a dropping funnel and was added slowly to the cooled reaction mixture for approximately 15 min. As the addition of the glyoxylic acid proceeded, the reaction mixture became cloudy and the flask became warm. The mixture was allowed to stir for 10 min after the addition. When the reaction was complete, the water generated during the reaction was removed. The organic layer was dried over Na2SO4, filtered via Buchner funnel, rinsed with toluene, concentrated in vacuo to yield an oil which was used directly in the next step.
Workup
- customequipped a stirrer bar
- additionwas added slowly to the cooled reaction mixture for approximately 15 min
- temperaturethe flask became warm
- stirringto stir for 10 min
- additionafter the addition
- customwas removed
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered via Buchner funnel
- washrinsed with toluene
- concentrationconcentrated in vacuo
- customto yield an oil which
Sources & evidence
- ORD record
- ord-a00c6d6ac8a34941bfd8680d20d7c68b
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06440417B1
Reaction notes
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