Carbon Dioxide → HCID 86744840, compound

HRID 1493655Notes

Reaction equation

HRID 1493655 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>CN1CCC(O)C1.CCOCC.C(N(CC)CC)C.CC(C)=O>[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[CH2:6][CH2:7][N:10]([CH3:14])[CH2:11]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 3

HCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 86744840HCID 86744840, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent2×HCID 930741-Methyl-3-pyrrolidinolSolvent2×

Procedure

A solution of mitomycin A (100 mg) in 2 ml of 1-methyl-3-pyrrolidinol was stirred at room temperature and under nitrogen for 30 minutes with 500 mg of a 1.6% solution of KOH in 1-methyl-3-pyrrolidinol. The reaction mixture was diluted with ether and then decomposed with dry ice. The ether was removed under reduced pressure and the residue left was isolated twice on silica gel using triethylamine as a solvent in the first isolation and 4% of triethylamine in acetone in the second isolation. In both isolation processes the pink substance was extracted from the silica gel with a mixture of triethylamine-acetone 1:3 or 1:4. The extract was concentrated under reduced pressure to give 50 m (42%) of the title compound, having no definite melting point and providing the following analysis:

Workup

  1. customThe ether was removed under reduced pressure
  2. waitthe residue left
  3. customwas isolated twice on silica gel
  4. extractionwas extracted from the silica gel with a mixture of triethylamine-acetone 1:3 or 1:4
  5. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c07fbec2e3364f5d933e43021948aa03
Source dataset
uspto-grants-1991_06
Patent number
US05023253

Reaction notes

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