Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | (3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one | HCID 12590460 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 13232653 | HCID 13232653 | 77.2% |
Reaction Steps
To a solution of 12.3 g of (3R, 4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone in 150 ml of DMF is added a solution of 1.6 g of potassium cyanide in 24 ml of water under ice-cooling and the mixture is stirred at room temperature (approx. 25° C.) for 30 minutes. To the reaction mixture are added ice water and ethyl acetate, and the ethyl acetate layer is taken, washed with water and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is chromatographed on a silica gel column [eluant: ethyl acetate-n-hexane (1:1)] to give 6.7 g of (3S, 4RS)-4-cyano-3-tritylamino-2-azetidinone (4R:4S=1:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04684724 |
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| Source dataset | uspto-grants-1987_08 |
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| ORD ID | ord-9b042347b36c4a3287150473876816b6 |
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| Source note | uspto-grants-1987_08 |
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