Carbon Dioxide → HCID 86744842, compound

HRID 1493656Notes

Reaction equation

HRID 1493656 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.[CH3:31][S:32][CH2:33]CO>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][CH2:25][CH2:31][S:32][CH3:33])=[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 14797Potassium HydroxideHCID 19972Mitomycin AHCID 789252-(Methylthio)ethanol2×

Product 1

HCID 86744842HCID 86744842, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of mitomycin A (100 mg) in 2 ml of 2-(methylthio)ethanol was stirred at room temperature under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in 2-(methylthio)ethanol. The reaction mixture was diluted with ether and decomposed with dry ice. Components in the etherial solution were separated on a silica gel column using ether as a solvent, which elutes the 2-(methylthio)ethanol, followed by a mixture of chloroform and methanol 9:1 or 8:2, which elutes the product. The product was further purified by preparative thin layer chromatography on silica gel with a mixture of chloroform and methanol 9:1. This procedure gave 85 mg (72%) of the title compound, having a melting point of 72°-86° C. (decomposition) and providing the following analysis:

Workup

  1. customComponents in the etherial solution were separated on a silica gel column
  2. additionfollowed by a mixture of chloroform and methanol 9:1 or 8:2, which
  3. customThe product was further purified by preparative thin layer chromatography on silica gel with a mixture of chloroform and methanol 9:1

Sources & evidence

ORD record
ord-89fc9ef57ece43f6afa61807dedd56c8
Source dataset
uspto-grants-1991_06
Patent number
US05023253

Reaction notes

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