Carbon Dioxide → HCID 86743612, compound

HRID 2372443Notes

Reaction equation

HRID 2372443 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.[CH2:31]1[O:33][CH:32]1CO>>[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][CH2:25][CH:32]3[O:33][CH2:31]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

5

Reactant 4

HCID 280Carbon DioxideHCID 11164Glycidol2×HCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 86743612HCID 86743612, compoundYield 33%

Procedure

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of glycidol was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in glycidol. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The crude reaction product was chromatographed on a silica gel column using first CHCl3 -MeOH 9.5:0.5, which elutes glycidol and pink by-products, and then CHCl3 -MeOH 9:1, which elutes the product. The product was further purified by preparative thin layer chromatography on silica gel with a mixture of CHCl3 and methanol 9:1 as the solvent. Thus, there was obtained 712 mg (33%) of the desired product, which gave indefinite decomposition on heating and provided the following compound analysis:

Workup

  1. customat room temperature
  2. customThe crude reaction product
  3. customwas chromatographed on a silica gel column
  4. customThe product was further purified by preparative thin layer chromatography on silica gel with a mixture of CHCl3 and methanol 9:1 as the solvent

Sources & evidence

ORD record
ord-0e8cbe4096694d64abbd054a574e8ce6
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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