HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → N-(3-methoxycarbonyl-2-methylpropanoyl)-L-alanine benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 4-Methyl hydrogen 2-methylenesuccinate | HCID 81791 | — |
| Reactant | benzyl (2S)-2-aminopropanoate | HCID 726858 | — |
| Reactant | 4-Methoxy-2-methyl-4-oxobutanoic acid | HCID 4563901 | — |
| Reactant | HCID 178418300 | HCID 178418300 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-(3-methoxycarbonyl-2-methylpropanoyl)-L-alanine benzyl ester | HCID 53826083 | — |
Reaction Steps
L-alanine benzyl ester (44.7 g.) and hydroxybenzotriazole (34 g.) are dissolved in dioxane (750 ml.) and the solution is chilled with stirring in an ice-water bath. Dicyclohexylcarbodiimide (51.5 g.) and 3-methoxycarbonyl-2-methylpropanoic acid (36 g.), prepared by hydrogenation of 3-methoxycarbonyl-2-methylene propanoic acid, are added in that order and the mixture is stirred at room temperature for 18 hours. The precipitate is filtered off, and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in ethyl acetate and washed neutral. The ethyl acetate is dried over magnesium sulfate and concentrated to dryness in vacuo to yield N-(3-methoxycarbonyl-2-methylpropanoyl)-L-alanine benzyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04105789 |
| Source dataset | uspto-grants-1978_08 |
| ORD ID | ord-731eb7e5214c4a97a664ce08cfb7fc56 |
| Source note | uspto-grants-1978_08 |