Mitomycin A → HCID 20138629, compound

HRID 1253111Notes

Reaction equation

HRID 1253111 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]=1OC)[C@H:13]1[NH:23][C@H:12]1[CH2:11]3.[NH:26]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]1>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]([N:26]3[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]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

4

Reactant 2

HCID 19972Mitomycin AHCID 982104-Hydroxypyrrolidine

Product 1

HCID 20138629HCID 20138629, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of mitomycin A (50 mg) in 6 ml of anhydrous methanol was treated with 3-pyrrolidinol (13 mg) under nitrogen at room temperature. When thin-layer chromatography on silica gel (2:8 methanol-chloroform as solvent) showed that starting material no longer was present, the mixture was filtered and evaporated under reduced pressure. The residue was purified by preparative thinlayer chromatography using the same solvent system. This procedure gave 23 mg (40% yield) of the desired product having a melting point of 82°-85° C. (decomposition) and providing the following analysis:

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by preparative thinlayer chromatography

Sources & evidence

ORD record
ord-ce0add85673c49fd8a8797d687b8f55c
Source dataset
uspto-grants-1988_05
Patent number
US04746746

Reaction notes

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