Carbon Dioxide → HCID 86743610, compound

HRID 477563Notes

Reaction equation

HRID 477563 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]([O:33][CH2:34][CH2:35][O:36][CH2:37]CO)[CH3:32]>C(Cl)(Cl)Cl.CO>[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][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:31][CH3:32])=[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 4

HCID 280Carbon DioxideHCID 8146Diethylene Glycol Monoethyl Ether2×HCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 86743610HCID 86743610, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of diethylene glycol monoethyl ether was stirred at room temperature and under nitrogen for 45 minutes with 480 mg of a 1.6% solution of KOH in diethylene glycol monoethyl ether. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. It was then isolated on a silica gel column using CHCl3 -MeOH 9:1 as solvent. Final purification was achieved by preparative thin layer chromatography on silica gel with a mixture of CHCl3 -MeOH 9:1. This procedure resulted in 80 mg (62%) of the title compound, having a melting point of 140°-143° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customIt was then isolated on a silica gel column
  3. customFinal purification
  4. additionwas achieved by preparative thin layer chromatography on silica gel with a mixture of CHCl3 -MeOH 9:1

Sources & evidence

ORD record
ord-7729117df01a4f1fb48c93bbe9c7e917
Source dataset
uspto-grants-1989_12
Patent number
US04888341

Reaction notes

Loading…