Pyridine → (4R)-2-oxo-3-benzylthiazolidin-4-carbaldehyde
Reaction equation
[CH2:1]([N:8]1[C@H:12]([CH2:13][OH:14])[CH2:11][S:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O.C(OCC)(=O)C>[O:15]=[C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:12]([CH:13]=[O:14])[CH2:11][S:10]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
In 45 ml of dimethylsulfoxide was dissolved 20 g of (4R)-3-benzyl-4-hydroxymethylthiazolidin-2-one under room temperature, 1.45 ml of pyridine, 1.38 ml of trifluoroacetic acid, and 30 ml of ethyl acetate were added to the solution in this order. At 25° C., 22.2 g of dicyclohexylcarbodiimide and 15 ml of ethyl acetate were added to the above mixture, and the resulting mixture was stirred at 50° C. for 3 hours. To the reaction mixture was added 100 ml of ethyl acetate, the mixture was stirred at 10° C. or lower for 30 minutes, and precipitated product was filtered off. The filtrate was washed with brine (saturated brine:water=1:1), and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, washed with brine (saturated brine:water=1:1), dried, and concentrated to obtain (4R)-2-oxo-3-benzylthiazolidin-4-carbaldehyde.
Workup
- stirringthe mixture was stirred at 10° C. or lower for 30 minutes
- customprecipitated product
- filtrationwas filtered off
- washThe filtrate was washed with brine (saturated brine:water=1:1)
- extractionthe aqueous layer was further extracted with ethyl acetate
- washwashed with brine (saturated brine:water=1:1)
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1487f85d12a0424ab728b83c024fc024
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335778B2
Reaction notes
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