Acetone → HCID 86744838, compound

HRID 1493654Notes

Reaction equation

HRID 1493654 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.CC(C)=O.OC[CH2:37][N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>C(N(CC)CC)C>[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][CH2:37][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]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

7

Reactant 5

HCID 180AcetoneHCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 19972Mitomycin AHCID 762881-Pyrrolidineethanol2×

Product 1

HCID 86744838HCID 86744838, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of mitomycin A (100 mg) in 4 ml of 1-(2-hydroxyethyl)pyrrolidine was stirred at room temperature and under nitrogen for 45 minutes with 240 mg of a 1.6% solution of potassium hydroxide in 1-(2-hydroxyethyl)pyrrolidine. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The reaction product was isolated twice on silica gel plate using triethylamine as a solvent in the first isolation and acetone in the second isolation. The pink band was cut and extracted with a mixture of acetone-triethylamine (4:1). The extract was concentrated under reduced pressure to give 40 mg (32%) of the title compound, having no definite melting point and providing the following analysis:

Workup

  1. customat room temperature
  2. customThe reaction product was isolated twice on silica gel plate
  3. extractionextracted with a mixture of acetone-triethylamine (4:1)
  4. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1165822fbaee4dea9fc2dffbad8077b9
Source dataset
uspto-grants-1991_06
Patent number
US05023253

Reaction notes

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