Carbon Dioxide → HCID 19904337, compound

HRID 2372447Notes

Reaction equation

HRID 2372447 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)C=C.[Cl:35][CH2:36][CH2:37]CO>C(Cl)(Cl)Cl.CO.CCOCC>[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][CH2:37][CH2:36][Cl:35])=[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

8

Reactant 5

HCID 280Carbon DioxideHCID 7858Allyl AlcoholHCID 123133-Chloro-1-propanol2×HCID 14797Potassium HydroxideHCID 19972Mitomycin A

Product 1

HCID 19904337HCID 19904337, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584188Chloroform methanolSolvent

Procedure

A solution of mitomycin A (100 mg) in 4 ml of 3-chloropropanol was stirred at room temperature and under nitrogen for 45 minutes with 240 mg of a 1.6% solution of KOH in 3-chloropropanol. 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 allyl alcohol to the top of the plate (the plate was developed several times), followed by a mixture of chloroform-methanol 9:1 which elutes the product. This procedure gives 75 mg (64%) of the desired product, having a melting point of 142°-145° 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-af0edb888f644065ab96fc3d6300f72f
Source dataset
uspto-grants-1992_03
Patent number
US05098926

Reaction notes

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