Carbon Dioxide → HCID 86744846, compound

HRID 1493658Notes

Reaction equation

HRID 1493658 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([O:21][CH3:22])([C@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C:6]=2[C:4](=[O:5])[C:3]=1[O:24][CH3:25])[C@H:13]1[NH:23][C@H:12]1[CH2:11]3.[OH-].[K+].C(=O)=O>OC1CCN(C)CC1.CCOCC>[C:18](=[O:17])([OH:19])[NH2:20].[OH:17][CH2:16][CH:15]1[C:6]2[C:4](=[O:5])[C:3]([O:24][CH:25]3[CH2:12][CH2:11][N:10]([CH3:14])[CH2:7][CH2:6]3)=[C:2]([CH3:1])[C:8](=[O:9])[C:7]=2[N:10]2[CH2:11][CH:12]3[NH:23][CH:13]3[C:14]12[O:21][CH3:22]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 86744846HCID 86744846, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 660484-Piperidinol, 1-methyl-Solvent2×

Procedure

A solution of mitomycin A (100 mg) in 2 ml of 4-hydroxy-1-methylpiperidine was stirred at room temperature under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in 4-hydroxy-1-methylpiperidine. The reaction mixture was diluted with ether, then decomposed with dry ice. Components of etherial solution were separated on a silica gel column using triethylamine, which elutes the 4-hydroxy-1-methylpiperidine, and then a mixture of acetone-triethylamine 2:1, which elutes the product. The product was further purified by preparative thin layer chromatography on silica gel with a mixture of chloroform-methanol 7:3. This procedure gave 55 mg (44%) of the title compound, having a melting point of 47°-65° C. (decomposition) and providing the following analysis:

Workup

  1. customComponents of etherial solution were separated on a silica gel column
  2. additiona mixture of acetone-triethylamine 2:1, which
  3. customThe product was further purified by preparative thin layer chromatography on silica gel with a mixture of chloroform-methanol 7:3

Sources & evidence

ORD record
ord-53a4b929ac6945e9aa3bfd621edd3d60
Source dataset
uspto-grants-1991_06
Patent number
US05023253

Reaction notes

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