Amsacrine → m-AMSA D-gluconate

HRID 246841

Reaktionsgleichung

Reaktionsgleichung von HRID 246841
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12.[O:29]=[C:30]([OH:41])[C@@H:31]([C@H:33]([C@@H:35]([C@@H:37]([CH2:39][OH:40])[OH:38])[OH:36])[OH:34])[OH:32].O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=12.[O:29]=[C:30]([O-:41])[C@@H:31]([C@H:33]([C@@H:35]([C@@H:37]([CH2:39][OH:40])[OH:38])[OH:36])[OH:34])[OH:32]

Komponenten

4

Edukt 2

HCID 2179AmsacrineHCID 72206655(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid hydrate

Produkt 1

HCID 86738977m-AMSA D-gluconateAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3.93 gm of m-AMSA and 5.15 gm of D-gluconic acid-water solution (38% w/w) in 305 ml of specially denatured 3A anhydrous ethanol at 70°-80° C. is filtered with suction. The filtrate is cooled to 30°-35° C. and 100 ml of anhydrous diethyl ether is added with stirring. After chilling to 0°-5° C. with stirring, the mixture is stored about 16 hours at 5° C. The product is collected, washed with specially denatured 3A anhydrous ethanol and anhydrous diethyl ether (3:1) at 5° C., then with several portions of anhydrous ether and dried under reduced pressure at 50°-55° C. to give 3.95 gm of m-AMSA D-gluconate. The salt obtained by this process retains a small amount (about 1% of ethanol).

Aufarbeitung

  1. customat 70°-80° C.
  2. filtrationis filtered with suction
  3. temperatureThe filtrate is cooled to 30°-35° C.
  4. addition100 ml of anhydrous diethyl ether is added
  5. temperatureAfter chilling to 0°-5° C.
  6. stirringwith stirring
  7. customThe product is collected
  8. washwashed
  9. customat 5° C.
  10. dry with materialwith several portions of anhydrous ether and dried under reduced pressure at 50°-55° C.

Quellen und Nachweise

ORD-Eintrag
ord-d2c2b98707a2429f9c6f648a4fbbed16
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04704397

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