Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | 1,2-Epoxydodecane | HCID 17858 | — |
| Edukt | (3S)-3-amino-3-phenylpropanoic acid | HCID 686704 | — |
| Edukt | Sodium Methoxide | HCID 10942334 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Produkt | HCID 66661964 | HCID 66661964 | 87,9% |
Reaktionsschritte
27.01 g of sodium methoxide and 82.6 g of (S)-3-amino-3-phenylpropionic acid were dissolved in 800 ml of methanol. After adding 92 g of 1,2-epoxydodecane, the solution was stirred at room temperature for 20 h. Subsequently, the pH of the solution was adjusted to pH 6 with methanolic hydrochloric acid and the sodium chloride which crystallized out filtered off. After the methanol was distilled off, an oily residue remained, which crystallized in the course of stirring with 700 ml of acetone. This resulted in 153.4 g of colorless crystals. 1H NMR (DMSO) δ (ppm): 0.85 (t, 3H), 1.13-1.31 (m, 18H), 2.28/2.60/2.70/2.86 (m, 2H), 3.02 (m, 1H), 3.34 (m, 1H), 3.66-3.78 (m, 1H), 4.57 (m, 1H), 5.20/5.29 (s, br., 1H, OH), 7.42 (m, 3H), 7.60 (m, 2H), 9.40 (s, br., 2H, NH2+), 12.56 (s, 1H, CO2H)
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08647882B2 |
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| Quelldatensatz | uspto-grants-2014_02 |
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| ORD ID | ord-301adbb9d4b9442e98ab170d47998e12 |
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| Quellennotiz | uspto-grants-2014_02 |
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