Chlorambucil → Prednimustine

HRID 485633

Reaktionsgleichung

[CH3:1][C@@:2]12[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:16][CH2:17][C:18]3[C@@:24]([CH3:25])([C@H:5]1[C@@H:4]([OH:26])[CH2:3]2)[CH:23]=[CH:22][C:20](=[O:21])[CH:19]=3.[CH:27]1[C:32]([CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])=[CH:31][CH:30]=[C:29]([N:39]([CH2:43][CH2:44][Cl:45])[CH2:40][CH2:41][Cl:42])[CH:28]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(O)(=O)C>[CH3:1][C@@:2]12[C@@:10]([OH:15])([C:11]([CH2:13][O:14][C:36]([CH2:35][CH2:34][CH2:33][C:32]3[CH:27]=[CH:28][C:29]([N:39]([CH2:40][CH2:41][Cl:42])[CH2:43][CH2:44][Cl:45])=[CH:30][CH:31]=3)=[O:37])=[O:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:16][CH2:17][C:18]3[C@@:24]([CH3:25])([C@H:5]1[C@@H:4]([OH:26])[CH2:3]2)[CH:23]=[CH:22][C:20](=[O:21])[CH:19]=3

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To 250 ml CH2Cl2 is added with stirring 36 g prednisolone (0.10 mol), 31.3 g chlorambucil (0,103 mol), 1.2 g DMAP (0,01 mol) and 1.1 g pTSA (0,06 mol). The reaction mixture is cooled to 0° C. and with continued stirring at this temperature a solution of 22.7 g DCC (0,11 mol) in 50 ml CH2Cl2 is slowly added. The reaction mixture is then kept at 0° C. with stirring for 20 h. 3 ml acetic acid is added and precipitated urea filtered off. The filtrate is evaporated in vacuo and the residue recrystallized from ethanol to give 58.9 g of TLC pure prednimustine (91% yield) without any discolouration. M.P. 165°-166° C.

Aufarbeitung

additionis slowly added
customis then kept at 0° C.
customprecipitated urea
filtrationfiltered off
customThe filtrate is evaporated in vacuo
customthe residue recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-55fd81bfd4974c2a87c86e5c323af55e
Quelldatensatz: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04537722

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