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

HRID 477567

Reaction equation

HRID 477567 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.[OH:31][CH2:32][CH2:33][S:34][S:35][CH2:36]CO>>[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][CH2:36][S:35][S:34][CH2:33][CH2:32][OH:31])=[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

5

Reactant 4

HCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 15906Hydroxyethyl disulfide2×HCID 19972Mitomycin A

Product 1

HCID 199043411,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-[2-(2-hydroxyethyldithio)ethoxy]azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamateYield 44%

Procedure

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of 2-hydroxyethyldisulphide was stirred at room temperature and under nitrogen for 45 minutes with 240 mg of a 1.6% solution of KOH in 2-hydroxyethyldisulphide. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The reaction mixture was chromatographed on a silica gel column using CHCl3 -acetone 1:1 and the CHCl3 -MeOH 9:1 as solvent systems. The product was further purified by preparative thin layer chromatography on silica gel using CHCl3 -acetone 3:7. Thus, there was obtained 23 mg (44%) of the desired product, having a melting point of 87°-95° C. (decomposition) and providing the following analysis:

Workup

  1. customat room temperature
  2. customThe reaction mixture was chromatographed on a silica gel column
  3. customThe product was further purified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-a9d063eaefdf4b3faba0b0e699159c4b
Source dataset
uspto-grants-1989_12
Patent number
US04888341

Linked notes

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