Chloroform → 77327-04-9

HRID 2412669Notes

Reaction equation

HRID 2412669 reaction equation
[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]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 13895197HCID 13895197, compound

Product 1

HCID 12384477327-04-9

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cf80f4ebcb8f48fab17c428be9959ea4
Source dataset
uspto-grants-1985_01
Patent number
US04493796

Reaction notes

Loading…