Dimethyl Sulfoxide → [4-((R)-2-formyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetic acid methyl ester
Reaction equation
CCN=C=NCCCN(C)C.[CH3:12][O:13][C:14](=[O:30])[CH2:15][O:16][CH2:17][C:18]#[C:19][CH2:20][N:21]1[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C@@H:22]1[CH2:28][OH:29].CS(C)=O.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:12][O:13][C:14](=[O:30])[CH2:15][O:16][CH2:17][C:18]#[C:19][CH2:20][N:21]1[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C@@H:22]1[CH:28]=[O:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
EDCI (214 mg, 1.12 mmol) was added to a solution of [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetic acid methyl ester (100 mg, 0.37 mmol) in benzene (3.5 mL). The reaction mixture was cooled to 0° C. and DMSO (0.11 mL, 1.55 mmol) was added. After 5 min at 0° C., pyridinium trifluoroacetate (79 mg, 0.41 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 3 h. The solution was decanted from the oily residue and the residue was washed with benzene (3×3 mL). The combined benzene phases were concentrated in vacuo to afford crude [4-((R)-2-formyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetic acid methyl ester, which was used without further purification.
Workup
- temperatureto warm to rt
- customThe solution was decanted from the oily residue
- washthe residue was washed with benzene (3×3 mL)
- concentrationThe combined benzene phases were concentrated in vacuo
Sources & evidence
- ORD record
- ord-0947a034674d4689ad14d1c6a6498a28
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326716B2
Reaction notes
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