Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | N-((Phenylmethoxy)carbonyl)-S-(phenylmethyl)-L-cysteine | HCID 98775 | — |
| Reactant | Glycine ethyl ester, hydrochloride | HCID 2723640 | — |
| Reactant | Methanesulfonic acid, 1H-benzotriazol-1-yl ester | HCID 11745953 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57190921 | HCID 57190921 | 58% |
Reaction Steps
N-Benzyloxycarbonyl-S-benzyl-L-cysteine (1.73 g) and glycine ethyl ester hydrochloride (0.70 g) are suspended into chloroform (20 ml) and therein is dissolved triethylamine (1.4 ml). To the solution is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.07 g) with stirring under ice-cooling. The mixture is stirred for 2 hours and then allowed to stand overnight. To the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is separated and 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 petroleum ether to give N-(N-benzyloxycarbonyl-S-benzyl-L-cysteinyl)glycine ethyl ester (1.25 g), melting pont: 89°-93° 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-7782070c44144ae29add4b8b6cefe5b4 |
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| Source note | uspto-grants-1980_12 |
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