Ethyl acetimidate → Butyric Acid

HRID 478937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478937
[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@@H:9]2[O:14][C@H:13]([CH2:15][NH2:16])[C@H:12]([OH:17])[C@@H:11]([OH:18])[C@H:10]2[NH2:19])[C@H:4]([O:20][C@@H:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([O:28][C@H:29]3[O:34][C@@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]3[NH2:39])[C@H:22]2[OH:40])[C@@H:3]([OH:41])[C@@H:2]1[NH2:42].N[CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48].C(=N)(OCC)C>C(O)C>[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@@H:9]2[O:14][C@H:13]([CH2:15][NH2:16])[C@H:12]([OH:17])[C@@H:11]([OH:18])[C@H:10]2[NH2:19])[C@H:4]([O:20][C@@H:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([O:28][C@H:29]3[O:34][C@@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]3[NH2:39])[C@H:22]2[OH:40])[C@@H:3]([OH:41])[C@@H:2]1[NH2:42].[C:47]([OH:49])(=[O:48])[CH2:46][CH2:45][CH3:44]

Komponenten

5

Edukt 2

HCID 65066Ethyl acetimidateHCID 131724201neomycin B gamma-amino butyric acid

Produkt 2

HCID 264Butyric AcidHCID 70685100(2R,3R,4S,5R,6S)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

For acetamidylation, the neomycin B/γ-amino butyric acid conjugate obtained in Example 9a above is treated with O-ethyl acetimidate in absolute ethanol for 1-2 days, resulting in acetimidylation of the terminal amino groups. The product is purified by ion exchange chromatography, yielding neomycin B/N-acetamidino butyric acid conjugate 16.

Aufarbeitung

  1. customresulting in acetimidylation of the terminal amino groups
  2. customThe product is purified by ion exchange chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7319a3cd3d904407a8fff9182bd64d24
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642365B1

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