Chloroform → didemnins

HRID 2412669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2412669
[CH3:1][CH2:2][C@@H:3]([C@H:5]1[NH:37][C:35](=[O:36])[C@@H:34]([NH:38][C:39]([C@H:41]([N:46](C([C@H]2N(C(C(O)C)=O)CCC2)=O)[CH3:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:40])[C@@H:33]([CH3:60])[O:32][C:30](=[O:31])[C@H:29]([CH2:61][C:62]2[CH:63]=[CH:64][C:65]([O:68][CH3:69])=[CH:66][CH:67]=2)[N:28]([CH3:70])[C:26](=[O:27])[C@H:25]2[N:21]([CH2:22][CH2:23][CH2:24]2)[C:19](=[O:20])[C@H:18]([CH2:71][CH:72]([CH3:74])[CH3:73])[NH:17][C:15](=[O:16])[C@@H:14]([CH3:75])[C:12](=[O:13])[C@H:11]([CH:76]([CH3:78])[CH3:77])[O:10][C:8](=[O:9])[CH2:7][C@@H:6]1[OH:79])[CH3:4].C(Cl)(Cl)Cl>CO>[CH3:1][CH2:2][C@@H:3]([C@H:5]1[NH:37][C:35](=[O:36])[C@@H:34]([NH:38][C:39]([C@H:41]([NH:46][CH3:47])[CH2:42][CH:43]([CH3:44])[CH3:45])=[O:40])[C@@H:33]([CH3:60])[O:32][C:30](=[O:31])[C@H:29]([CH2:61][C:62]2[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=2)[N:28]([CH3:70])[C:26](=[O:27])[C@H:25]2[N:21]([CH2:22][CH2:23][CH2:24]2)[C:19](=[O:20])[C@H:18]([CH2:71][CH:72]([CH3:74])[CH3:73])[NH:17][C:15](=[O:16])[C@@H:14]([CH3:75])[C:12](=[O:13])[C@H:11]([CH:76]([CH3:78])[CH3:77])[O:10][C:8](=[O:9])[CH2:7][C@@H:6]1[OH:79])[CH3:4]

Komponenten

4

Edukt 2

HCID 6212ChloroformHCID 13895197HCID 13895197, Verbindung

Produkt 1

HCID 123844didemnins

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A similar isolation scheme was employed later during large scale production of didemnin B for biological testing. The dichloromethane extract was obtained as before with only minor modifications due to scale-up. Prep LC employed an isocratic chloroform:methanol solvent system ranging from 98:2 to 96:4 depending on the condition of the reusable PrepPak cartridge. This allowed the use of the built-in refractive index detector to monitor elution of the didemnins. Fractions obtained through this procedure were chromatographed on a reversed phase (ODS) PrepPak cartridge with 77:23 methanol:water, again monitoring with the refractive index detector. Pooling of the appropriate fractions gave yields of didemnins A-C similar to those obtained with the original procedure. Didemnins D and E could only be separated by HPLC as above.

Aufarbeitung

  1. extractionThe dichloromethane extract
  2. customwas obtained as before with only minor modifications due
  3. washelution of the didemnins
  4. customFractions obtained through this procedure
  5. customwere chromatographed on a reversed phase (ODS) PrepPak cartridge with 77:23 methanol
  6. customPooling of the appropriate fractions gave

Quellen und Nachweise

ORD-Eintrag
ord-cf80f4ebcb8f48fab17c428be9959ea4
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04493796

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