Hydrochloric Acid → 7-demethylmitomycin A

HRID 1194488

Reaktionsgleichung

Reaktionsgleichung von HRID 1194488
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([O:21][CH3:22])([C@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C:6]=2[C:4](=[O:5])[C:3]=1N)[C@H:13]1[NH:23][C@H:12]1[CH2:11]3.Cl.CCCCCC.[OH-:32].[Na+]>CCOCC>[CH3:1][C:2]1[C:3](=[O:32])[C:4](=[O:5])[C:6]2[C@@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C@@:14]3([O:21][CH3:22])[C@H:13]4[NH:23][C@H:12]4[CH2:11][N:10]3[C:7]=2[C:8]=1[OH:9]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 5746Mitomycin CHCID 8058HexaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 117273937-demethylmitomycin AAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Mitomycin C (2.2 g, 6.6 mmoles) was dissolved in 140 ml 0.1N methanolic NaOH (50%) and the reaction mixture was stirred at room temperature for 30 hours. The solution was then adjusted to ca. pH 4.0 with 1N HCl and extracted with ethyl acetate (4×500 ml). The combined ethyl acetate extracts were dried (Na2SO4) and evaporated under reduced pressure at about 30° to 35° C. to obtain a solid residue, which upon dissolving in ether and treating with excess hexane afforded a purple precipitate. The precipitate was collected and air dried to afford the title compound as a fine purple powder (1.4 g, 63%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (4×500 ml)
  2. dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
  3. customevaporated under reduced pressure at about 30° to 35° C.
  4. customto obtain a solid residue, which
  5. customafforded a purple precipitate
  6. customThe precipitate was collected
  7. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-6f6871a3142b48349932b79637e5274e
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04814445

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