Water → HCID 178493332, compound

HRID 887680Notes

Reaction equation

HRID 887680 reaction equation
O[C:2]1[C:11]2[C:10](=[O:12])[C:9]([O:13][CH3:14])=[CH:8][C:7](=[O:15])[C:6]=2[C:5]([OH:16])=[C:4]2[C:17](=[O:37])[C@:18]3([C:32]4[C:31]([OH:33])=[C:30]5[C:25]([CH:26]=[C:27]([CH:35]=O)[NH:28][C:29]5=[O:34])=[CH:24][C:23]=4[CH2:22][CH2:21]3)[C:19](=[O:20])[C:3]=12.[Cl-].[OH:39][NH3+:40].N1C=CC=CC=1.[OH2:47]>CN(C=O)C>[OH:47][C:2]1[C:11]2[C:10](=[O:12])[C:9]([O:13][CH3:14])=[CH:8][C:7](=[O:15])[C:6]=2[C:5]([OH:16])=[C:4]2[C:17](=[O:37])[C@:18]3([C:32]4[C:31]([OH:33])=[C:30]5[C:25]([CH:26]=[C:27]([CH:35]=[N:40][OH:39])[NH:28][C:29]5=[O:34])=[CH:24][C:23]=4[CH2:22][CH2:21]3)[C:19](=[O:20])[C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 21645Hydroxylamine HClHCID 178493334(8S)-4',9,9'-trihydroxy-6'-methoxy-1,1',3',5',8'-pentaoxospiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-3-carbaldehyde

Product 1

HCID 178493332HCID 178493332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ten (10) mg (19.4 μmol) fredericamycin aldehyde (4) are dissolved in 2 mL DMF. After addition of 3.1 mg (44.6 μmol) hydroxylammonium chloride, 3.2 μl pyridine are added. Stirring for 2 h at room temperature. The reaction mixture is added to 50 ml water and extracted 3 times with ethyl acetate. After drying and concentration, a deep red amorphous crystal powder was left (HPLC clean).

Workup

  1. additionare added
  2. extractionextracted 3 times with ethyl acetate
  3. customAfter drying
  4. concentrationconcentration
  5. waita deep red amorphous crystal powder was left (HPLC clean)

Sources & evidence

ORD record
ord-93e3b1d57b9442bfa4db85bd7a5ab4d4
Source dataset
uspto-grants-2012_08
Patent number
US08247424B2

Reaction notes

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