Hydrochloric Acid → HCID 19801050, compound

HRID 1646633Notes

Reaction equation

HRID 1646633 reaction equation
[CH3:1][C:2]([CH3:27])=[CH:3][CH2:4][C@H:5]1[O:7][C@@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([O:17][C:18]([NH:20][C:21]([CH2:23][Cl:24])=[O:22])=[O:19])[C@H:10]1[O:25][CH3:26])[CH3:8].[ClH:28]>CO>[Cl:24][CH2:23][C:21]([NH:20][C:18]([O:17][CH:11]1[CH2:12][CH2:13][C:14]([CH2:15][Cl:28])([OH:16])[CH:9]([C:6]2([CH3:8])[O:7][CH:5]2[CH2:4][CH:3]=[C:2]([CH3:1])[CH3:27])[CH:10]1[O:25][CH3:26])=[O:19])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 369976O-Chloroacetylcarbamoylfumagillol

Product 1

HCID 19801050HCID 19801050, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of O-(chloroacetylcarbamoyl)fumagillol (100 mg) in methanol (2 ml) was added 0.4N hydrochloric acid (1 ml), which was stirred for one hour at room temperatures. Resulting precipitates were collected by filtration and recrystallized from methanol-water to afford 4-O-(chloroacetylcarbamoyl)-2(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-chloromethyl-1,4-cyclohexanediol (96 mg, yield 90%) colorless crystals.

Workup

  1. customResulting
  2. customprecipitates
  3. filtrationwere collected by filtration
  4. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-43fda8c29139401182f0cfd8e8da23d2
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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