Water → HCID 178502631, compound

HRID 887681Notes

Reaction equation

HRID 887681 reaction equation
[OH:1][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-].[CH3:39][O:40][NH3+:41].N1C=CC=CC=1.O>CN(C=O)C>[CH3:39][O:40][N:41]=[CH:35][C:27]1[NH:28][C:29](=[O:34])[C:30]2[C:25]([CH:26]=1)=[CH:24][C:23]1[CH2:22][CH2:21][C@@:18]3([C:17](=[O:37])[C:4]4=[C:5]([OH:16])[C:6]5[C:7](=[O:15])[CH:8]=[C:9]([O:13][CH3:14])[C:10](=[O:12])[C:11]=5[C:2]([OH:1])=[C:3]4[C:19]3=[O:20])[C:32]=1[C:31]=2[OH:33]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 11639O-methylhydroxylammonium chlorideHCID 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 178502631HCID 178502631, 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 3.4 mg (40.7 μmol) O-methylhydroxylammonium chloride and 3.2 μl pyridine, the reaction mixture is stirred for 2 h at room temperature. Then, it is added to 100 ml water, and the supernatant is sucked off from the red precipitate (HPLC clean).

Sources & evidence

ORD record
ord-dff8ef2cb9414bce8c10e0fa7a7b71d8
Source dataset
uspto-grants-2012_08
Patent number
US08247424B2

Reaction notes

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