Ammonia → HCID 11455930, compound

HRID 556255Notes

Reaction equation

HRID 556255 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

The reaction of Step (1) is as shown below. Specifically, 150 mg of caprazamycin B were dissolved in 1.5 mL of N,N-dimethylformamide. To this solution, 1.5 mL of 28% aqueous ammonia were added and the resulting mixture was stirred at room temperature for 4 days for hydrolysis. The insoluble material developed in the reaction mixture was removed by filtration and the filtrate was concentrated. The resulting residue was washed with acetone and dried to afford 74.7 mg of caprazol as a colorless solid (99% yield).

Workup

  1. customThe reaction of Step (1)
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated
  4. washThe resulting residue was washed with acetone
  5. customdried

Sources & evidence

ORD record
ord-a77b7b62e0714b158a83de63badea1a7
Source dataset
uspto-grants-2011_11
Patent number
US08058247B2

Reaction notes

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