Carbon Dioxide → HCID 86743614, compound

HRID 2372444Notes

Reaction equation

HRID 2372444 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][CH2:32][O:33][CH2:34]C>OC1CCOC1.CO.C(Cl)(Cl)Cl>[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[CH2:31][CH2:32][O:33][CH2:34]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

8

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 86743614HCID 86743614, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 99603-Furanol, tetrahydro-Solvent3×

Procedure

A solution of mitomycin A (100 mg or 0.286 mmole) in a 4 ml of 3-hydroxy tetrahydrofuran was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in 3-hydroxy tetrahydrofuran. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The product was isolated twice on silica gel plates. In the first isolation, the solvent was ether, which elutes 3-hydroxy tetrahydrofuran while the pink product stayed on the base line. In the second isolation a mixture of chloroform and methanol 9:1 was used as solvent. This procedure resulted in 36 mg (31%) of the desired product, having a melting point of 68°-75° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customThe product was isolated twice on silica gel plates

Sources & evidence

ORD record
ord-0df112a574be4599bf53b39c456ba318
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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