Carbon Dioxide → 1,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(propargyloxy)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate

HRID 477561Notes

Reaction equation

HRID 477561 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.[CH3:31][CH2:32]OCC>C(O)C#C.C(Cl)(Cl)Cl.CC(C)=O>[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][C:31]#[CH:32])=[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 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 199043501,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(propargyloxy)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamateYield 31%

Reagents, catalysts & solvents 2

HCID 7859Propargyl alcoholSolvent3×HCID 15930782Chloroform acetoneSolvent

Procedure

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of propargyl alcohol was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in propargyl alcohol. 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 propargyl alcohol to the top of the plate (the plate was developed several times), followed by CHCl3 -acetone 1:1 which elutes the product. This procedure gives 33 mg (31%) of the title compound, having a melting point of 77°-80° 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-aafb46376295441281ae6e9e98d3bbae
Source dataset
uspto-grants-1989_12
Patent number
US04888341

Reaction notes

Loading…