Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-((Phenylmethoxy)carbonyl)-S-(phenylmethyl)-L-cysteine | HCID 98775 | — |
| Reactant | Glycine ethyl ester, hydrochloride | HCID 2723640 | — |
| Reactant | Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate | HCID 54531055 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57190921 | HCID 57190921 | 23.2% |
Reaction Steps
N-Benzyloxycarbonyl-S-benzyl-L-cysteine (1.73 g) and glycine ethyl ester hydrochloride (0.70 g) are dissolved in dimethylformamide (12 ml), and thereto are added triethylamine (1.40 ml) and further ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (1.1 g). The mixture is allowed to stand at room temperature for 14 hours. To the reaction mixture are added water and ethyl acetate, and the ethyl acetate layer is separated, washed with water, 1 N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and the resulting residue is crystallized from ethanol-petroleum ether, separated by filtration and dried to give N-(N-benzyloxycarbonyl-S-benzyl-L-cysteinyl)glycine ethyl ester (0.5 g), melting point: 93°-95° C. The product is identified with an authentic sample by infrared spectrum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04242507 |
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| Source dataset | uspto-grants-1980_12 |
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| ORD ID | ord-064a2f6225b94b07b4b12e5539e36376 |
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| Source note | uspto-grants-1980_12 |
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