Carbon Dioxide → HCID 19835794, compound

HRID 2372446Notes

Reaction equation

HRID 2372446 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.C(O)C=C.[CH3:35][O:36][CH2:37][CH2:38][O:39][CH2:40]CO>C(Cl)(Cl)Cl.CO.CCOCC>[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][CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40])=[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 280Carbon DioxideHCID 7858Allyl AlcoholHCID 8134Diethylene Glycol Monomethyl Ether2×HCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 19835794HCID 19835794, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584188Chloroform methanolSolvent

Procedure

A solution of mitomycin A (100 mg) in 4 ml of 2-(2-methoxyethoxy)ethanol was stirred at room temperature and under nitrogen for 45 minutes with 240 mg of a 1.6% solution of KOH in 2-(2-methoxyethoxy)ethanol. 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 allyl alcohol to the top of the plate (the plate was developed several times), followed by chloroform-methanol 9:1 which elutes the product. This procedure gives 72 mg (58%) of the desired compound, having a melting point of 102°-104° C. 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-1c9156b029ae473aa6e361279c863e2d
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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