Carbon Dioxide → HCID 19904348, compound

HRID 2372445Notes

Reaction equation

HRID 2372445 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>CN(C)CCO>[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][CH2:7][N:10]([CH3:14])[CH3:11])=[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 19904348HCID 19904348, compoundYield 137.4%

Reagents, catalysts & solvents 1

HCID 79022-(Dimethylamino)ethanolSolvent2×

Procedure

A solution of mitomycin A (200 mg) in 4 ml of N,N-dimethyl ethanolamine was stirred at room temperature and under nitrogen for 45 minutes with 480 mg of a 1.6% solution of KOH in N,N-dimethyl ethanolamine. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The crude reaction mixture was evaporated under reduced pressure. The residue was triturated with ether and the resulting solid was filtered off. This procedure produced 167 mg (71%) of crude product, which was crystallized from ether or ether-acetone (least amount of acetone) to give reddish brown crystals, having a melting point of 140°-143° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customThe crude reaction mixture
  3. customwas evaporated under reduced pressure
  4. customThe residue was triturated with ether
  5. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-1ddd460e2f94425ea29220b27a89b6f4
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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