Ethyl cysteinate hydrochloride → Ethyl L-cysteinate

HRID 2286833

Reaktionsgleichung

Reaktionsgleichung von HRID 2286833
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3]>C(N(CC)CC)C>[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3]

Komponenten

3

Edukt 1

HCID 2723617Ethyl cysteinate hydrochloride

Produkt 1

HCID 13359Ethyl L-cysteinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Cysteine ethyl ester hydrochloride (11.2 g, 0.06 mole) was suspended in 40 ml of triethylamine with vigorous stirring for one hour at room temperature. The triethylamine hydrochloride was filtered and filtrate was concentrated to give cysteine ethyl ester as an oil. The oil was dissolved in 30 ml of pyridine and allowed to react with 3.2 g (0.01 mole) of progesterone at room temperature for 3.5 days. The suspension that resulted was filtered and crystallized from ethyl acetate to give 2.7 g (mp 162°-165° C., 47% yield) of the desired product: IR(KBr) 1740 cm-1 (s) (C=O); 1H NMR (CDCl3) δ5.23 (s, 1, CH=C), 4.2 (q, J=7 Hz, 4, CH3CH2O), 4.2-3.6 (m, 2, O2CCHN), 3.50-2.65 (m, 4, CH2S), 1.55 (s, 3, CH3 --C20), 1.3 (t, J=7 Hz, 6, CH3CH2O), 1.03 (s, 3, CH3 --C10), 0.85 (s, 3, CH3 --C13), 2.6-0.6 (m, 19, CH2 and CH); 13C NMR (CDCl3) δ171.88 and 171.99 (CO2), 148.86 (C5) and 122.89 (C4); [α]24.5 D-24.3° (C=0.63, CHCl3).

Aufarbeitung

  1. filtrationThe triethylamine hydrochloride was filtered
  2. concentrationfiltrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-83a7f8a1ed814233b584aba97f39a0f7
Quelldatensatz
uspto-grants-1981_05
Patentnummer
US04268441

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