Carbon Dioxide → HCID 86745574, compound

HRID 2372442Notes

Reaction equation

HRID 2372442 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:28](=[O:30])=O>O1CCCCC1CO>[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:4]3[CH2:3][CH2:2][CH2:1][CH2:28][O:30]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 3

HCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 86745574HCID 86745574, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 7524Tetrahydropyran-2-methanolSolvent2×

Procedure

A solution of mitomycin A (100 mg of 0.286 mmole) in 4 ml of tetrahydropyran-2-methanol was stirred at room temperature and under nitrogen for 45 minutes with 240 mg of a 1.6% solution of KOH in tetrahydropyran-2-methanol. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The reaction mixture was chromatographed on a silica gel column using CHCl3 and then CHCl3 -MeOH 9.5:0.5. The product was further purified by preparative thin layer chromatography (silica gel, CHCl3 -MeOH 9.5:0.5). Thus, there was obtained 57 mg (46%) of the desired product having a melting point of 135°-138° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customThe reaction mixture was chromatographed on a silica gel column
  3. customThe product was further purified by preparative thin layer chromatography (silica gel, CHCl3 -MeOH 9.5:0.5)

Sources & evidence

ORD record
ord-8554ce351cc24a8e910405118ea5e379
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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