HCID 57394089, compound → Caprazene

HRID 556254Notes

Reaction equation

HRID 556254 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

The reaction of Step (1) is as shown below. Specifically, 200 mg of caprazamycin B were dissolved in 6 mL of 80% aqueous acetic acid and the resulting solution was heated at 70° C. for 2 hours. Subsequently, the reaction mixture was concentrated and acetone was added to the syrup-like concentrate. The resulting precipitate was collected by filtration, washed with acetone and dried to afford 96.3 mg of caprazene as a colorless solid (99% yield).

Workup

  1. customThe reaction of Step (1)
  2. concentrationSubsequently, the reaction mixture was concentrated
  3. additionacetone was added to the syrup-like
  4. concentrationconcentrate
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-b76327ccf30149cd981f4682aea3d86c
Source dataset
uspto-grants-2011_11
Patent number
US08058247B2

Reaction notes

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