Ammonia → HCID 11455930, compound

HRID 2370672Notes

Reaction equation

HRID 2370672 reaction equation
C[C@@H]1O[C@@H](OC(C[C@H](CC(O[C@H](CC([O:36][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.N>CN(C)C=O>[CH3:75][N:39]1[C@@H:40]([C@H: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@H:44]([C:45]([OH:47])=[O:46])[C@@H:37]([OH:36])[CH2:38]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57394089HCID 57394089, compound

Product 1

HCID 11455930HCID 11455930, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Caprazamycin B (150 mg) was dissolved in N,N-dimethylformamide (1.5 ml), and to the resultant solution was then added 28% aqueous ammonia solution (1.5 ml). The resulting mixture was stirred at room temperature for 4 days to effect the intended hydrolysis. Insolubles formed in the reaction solution were filtered off, and thereafter the reaction solution was concentrated and the resulting residue was washed with acetone and dried. Thus, there was afforded caprazol (74.7 mg) as a colorless solid.

Workup

  1. customthe intended hydrolysis
  2. customInsolubles formed in the reaction solution
  3. filtrationwere filtered off
  4. concentrationthe reaction solution was concentrated
  5. washthe resulting residue was washed with acetone
  6. customdried

Sources & evidence

ORD record
ord-4aa2f38e959d49f8985f0729e38a47f2
Source dataset
uspto-grants-2014_04
Patent number
US08710198B2

Reaction notes

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