4-Methylmorpholine → HCID 178451297, compound

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Reaction Steps

To a mixture of the compound of Example I (0.60 g, 0.0018 mole) and CH2Cl2 (6 ml) was added N-methylmorpholine (0.44 g, 0.0043 mole). The resulting mixture was cooled on an ice bath and 3-benzoylthiopropanoyl chloride (0.45 g, 0.0020 mole) was added dropwise. After stirring 10 min the mixture was filtered removing the insolubles. The CH2Cl2 solution was washed with 20% citric acid, H2O, 10% NaHCO3, H2O and dried over MgSO4. The filtered solution was concentrated under reduced pressure to dryness and then azeotroped with diethyl ether to a semi-solid residue. This residue was dissolved in a small amount of diethyl ether and precipitated with hexane to give a crystalline solid. Drying in vacuo at 60° overnight gave 0.48 g (0.001 mole, 55%) of trans-N-(3-benzoylthio-1-oxopropyl)-N-(4-phenylcyclohexyl)glycine-1,1-dimethylethyl ester.

Provenance & Evidence