Carbon Dioxide → HCID 19835792, compound

HRID 477568Notes

Reaction equation

HRID 477568 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)=[O:29]>C(O)CO>[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][CH2:28][OH:29])=[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 19835792HCID 19835792, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent2×

Procedure

A solution of mitomycin A (200 mg) in 10 ml of ethylene glycol was stirred at room temperature and under nitrogen for 45 minutes with 480 mg of a 1.6% solution of KOH in ethylene glycol. 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 column packed with neutral alumina using CHCl3 -MeOH 8:2 as the solvent. This process separates the reaction products which are pink in color from ethylene glycol. The product from the pink fraction was rechromatographed on a silica gel plate with acetone to give two major bands. The product obtained from the second band was rechromatographed on a silica gel plate with a mixture of chloroform and methanol 9:1 to give the desired product. This procedure gave 64 mg (29%) of the desired product, having a melting point of 72°-74° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customThe reaction mixture was chromatographed on a column
  3. customThe product from the pink fraction was rechromatographed on a silica gel plate with acetone
  4. customto give two major bands
  5. customThe product obtained from the second band
  6. customwas rechromatographed on a silica gel plate with a mixture of chloroform and methanol 9:1

Sources & evidence

ORD record
ord-8c102c2b942e48cc819806baad387fde
Source dataset
uspto-grants-1989_12
Patent number
US04888341

Reaction notes

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