Carbon Dioxide → HCID 19904324, compound

HRID 2372441Notes

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)[CH:32]1[O:36][CH2:35][CH2:34][CH2:33]1>>[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][CH:35]3[O:36][CH2:32][CH2:33][CH2:34]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

Reactant 4

HCID 280Carbon Dioxide

HCID 7360Tetrahydrofurfuryl alcohol2×

HCID 14797Potassium Hydroxide

HCID 19972Mitomycin A

Product 1

HCID 19904324HCID 19904324, compoundYield 60%

Procedure

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of tetrahydrofurfuryl alcohol was stirred at room temperature and under nitrogen for 45 minutes with 480 mg of a 1.6% solution of KOH in tetrahydrofurfuryl alcohol. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The product was chromatographed on a silica gel column using CHCl3 -MeOH 9.5:0.5 as solvent. Further purification of the product was done by preparative thin layer chromatography (silica gel, CHCl3 -MeOH 9.5:0.5). This procedure resulted in 72 mg (60%) of the desired product having a melting point of 128°-133° C. (decomposition) and providing the following analysis:

Workup

customat room temperature
customThe product was chromatographed on a silica gel column
customFurther purification of the product

Sources & evidence

ORD record: ord-b5292913c2364e9caa6c9d9152739049
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098926

Reaction notes

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