Carbon Dioxide → HCID 19904335, compound

HRID 2372440Notes

Reaction equation

HRID 2372440 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.CCOCC.[CH:36]1(CO)[CH2:39][CH2:38][CH2:37]1>>[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][CH:36]3[CH2:39][CH2:38][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

6

Reactant 5

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 19972Mitomycin AHCID 78130Cyclobutylcarbinol3×

Product 1

HCID 19904335HCID 19904335, compoundYield 29%

Procedure

A solution of mitomycin A (64 mg) in 4 ml of cyclobutane methanol was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in cyclobutane methanol. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. It was then isolated on a silica gel plate using ether, which elutes the cyclobutane methanol to the top of the plate (the plate was developed several times). This procedure gives 21.5 mg (29%) of the title compound, having a melting point of 83°-88° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customIt was then isolated on a silica gel plate

Sources & evidence

ORD record
ord-d5d2249ae3b94e888aa0162773feb335
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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