Acetaldehyde → Netilmicin

HRID 1415073

Reaktionsgleichung

Reaktionsgleichung von HRID 1415073
S(=O)(=O)(O)O.[CH3:6][C@@:7]1([OH:36])[C@H:12]([NH:13][CH3:14])[C@@H:11]([OH:15])[C@@H:10]([O:16][C@@H:17]2[C@@H:22]([OH:23])[C@H:21]([O:24][C@H:25]3[O:30][C:29]([CH2:31][NH2:32])=[CH:28][CH2:27][C@H:26]3[NH2:33])[C@@H:20]([NH2:34])[CH2:19][C@H:18]2[NH2:35])[O:9][CH2:8]1.F[C:38](F)(F)[C:39](O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.P(=O)(O)(O)O.[N+]([O-])(O)=O.C(=O)C.C([BH3-])#N.[Na+]>O.C(O)(=O)C>[CH3:38][CH2:39][NH:35][C@H:18]1[C@H:17]([O:16][C@H:10]2[O:9][CH2:8][C@@:7]([OH:36])([CH3:6])[C@H:12]([NH:13][CH3:14])[C@H:11]2[OH:15])[C@@H:22]([OH:23])[C@H:21]([O:24][C@H:25]2[O:30][C:29]([CH2:31][NH2:32])=[CH:28][CH2:27][C@H:26]2[NH2:33])[C@@H:20]([NH2:34])[CH2:19]1

Komponenten

12

Edukt 9

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 6422Trifluoroacetic acidHCID 3611932385-11-8HCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 441306Netilmicin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

in the procedure of above Example 1A instead of adding 1 N sulfuric acid to the solution of sisomicin in water until it reaches a pH of about 5, other acids may be used, such as acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, hydrochloric acid, phosphoric acid, or nitric acid. The acidified aqueous solution is then treated with acetaldehyde and sodium cyanoborohydride and the resultant product is purified as described above, whereby is obtained 1-N-ethylsisomicin.

Aufarbeitung

  1. customthe resultant product is purified

Quellen und Nachweise

ORD-Eintrag
ord-1cf3e61ee5494d7a91ba96e414aab62f
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04002742

Verknüpfte Notizen

Wird geladen…