Acetone → HCID 86744836, compound

HRID 1493653Notes

Reaction equation

HRID 1493653 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.[O:35]1[CH2:40][CH2:39]C(O)[CH2:37][CH2:36]1>CCOCC.O1CCCC1>[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[CH2:39][CH2:40][O:35][CH2:36][CH2:37]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 5

HCID 180AcetoneHCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 19972Mitomycin AHCID 74956Tetrahydro-4H-pyran-4-ol2×

Product 1

HCID 86744836HCID 86744836, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent4×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of mitomycin A (100 mg) in 2 ml of tetrahydro-4H-pyran-4-ol was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in tetrahydro-4H-pyran-4-ol. The reaction mixture was diluted with a little ether and then decomposed with dry ice. Additional ether was added and the solid that deposited (42 mg) was filtered off and discarded. The pink filtrate was concentrated under reduced pressure and the residue was isolated twice on a silica gel plate, using 20% of tetrahydrofuran in ether as a solvent in the first isolation and 15% of acetone in ether in the second isolation. This procedure gave 25 mg (21%) of the title compound, having a melting point of 115°-120° C. (decomposition) and providing the following analysis:

Workup

  1. filtrationwas filtered off
  2. concentrationThe pink filtrate was concentrated under reduced pressure
  3. customthe residue was isolated twice on a silica gel plate

Sources & evidence

ORD record
ord-0999a066da23425396beb89790a1c9ce
Source dataset
uspto-grants-1991_06
Patent number
US05023253

Reaction notes

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