HCID 57394089, compound → Caprazene

HRID 2370671Notes

Reaction equation

HRID 2370671 reaction equation
C[C@@H]1O[C@@H](OC(C[C@H](CC(O[C@H](CC(O[C@@H:37]2[C@@H:44]([C:45]([OH:47])=[O:46])[N:43]([CH3:48])[C:41](=[O:42])[C@H:40]([C@H:49]([O:65][C@@H:66]3[O:70][C@H:69]([CH2:71][NH2:72])[C@@H:68]([OH:73])[C@H:67]3[OH:74])[C@H:50]3[O:54][C@@H:53]([N:55]4[C:61](=[O:62])[NH:60][C:58](=[O:59])[CH:57]=[CH:56]4)[C@H:52]([OH:63])[C@@H:51]3[OH:64])[N:39]([CH3:75])[CH2:38]2)=O)CCCCCCCCCCCC(C)C)=O)C)=O)[C@H](OC)[C@H](OC)[C@H]1OC>C(O)(=O)C>[CH3:75][N:39]1[C@@H:40]([CH:49]([O:65][C@@H:66]2[O:70][C@H:69]([CH2:71][NH2:72])[C@@H:68]([OH:73])[C@H:67]2[OH:74])[C@H:50]2[O:54][C@@H:53]([N:55]3[C:61](=[O:62])[NH:60][C:58](=[O:59])[CH:57]=[CH:56]3)[C@H:52]([OH:63])[C@@H:51]2[OH:64])[C:41](=[O:42])[N:43]([CH3:48])[C:44]([C:45]([OH:47])=[O:46])=[CH:37][CH2:38]1

Participants

3

Reactant 1

HCID 57394089HCID 57394089, compound

Product 1

HCID 68249819CaprazeneYield 100.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Caprazamycin B (200 mg) was dissolved in 80% aqueous acetic acid solution (6 ml) and the resulting solution was heated at 70° C. for 2 hours. The resulting reaction solution was concentrated, and to the resulting syrupy concentrate was added an amount of acetone. The precipitate so deposited was recovered by filtration, washed with acetone and dried. Thus, there was afforded caprazene (96.3 mg) as a colorless solid. Yield; 99%.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated
  3. concentrationto the resulting syrupy concentrate
  4. additionwas added an amount of acetone
  5. filtrationThe precipitate so deposited was recovered by filtration
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-25d461842d424ca8aad0c5158970e21e
Source dataset
uspto-grants-2014_04
Patent number
US08710198B2

Reaction notes

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