Carbon Dioxide → HCID 86744834, compound
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.[Cl:31][CH2:32][CH2:33][O:34][CH2:35]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][CH2:35][O:34][CH2:33][CH2:32][Cl: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
Procedure
A solution of mitomycin A (100 mg) in 2 ml of 2-(2-chloroethoxy)ethanol was stirred at room temperature and under nitrogen for 45 minutes with 300 mg of a 1.6% solution of KOH in 2-(2-chloroethoxy)ethanol. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The reaction product was chromatographed on a silica gel column using first chloroform, which elutes the 2-(2-chloroethoxy)ethanol and then acetone, which elutes the product. The latter was purified twice by preparative thin layer chromatography on silica gel using chloroform as a solvent in the first purification and chloroform-acetone 1:1 in the second purification. This procedure gave 74 mg (58%) of the title compound, having a melting point of 101°-104° C. (decomposition) and providing the following analysis:
Workup
- customat room temperature
- customThe reaction product was chromatographed on a silica gel column
- customThe latter was purified twice by preparative thin layer chromatography on silica gel
- customin the first purification and chloroform-acetone 1:1
- customin the second purification
Sources & evidence
- ORD record
- ord-90ee0fbb8782402490727550c711a9c6
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05023253
Reaction notes
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