HCID 69317962, compound → HCID 69316433, compound

HRID 2114853Notes

Reaction equation

HRID 2114853 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[C:23](=[O:24])[N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][CH:20]([C:33]([O:35][CH3:36])=[O:34])[C:11]=2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH2:1]([O:8][C:9]1[C:10]2[C:23](=[O:24])[N:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH:21]=[C:20]([C:33]([O:35][CH3:36])=[O:34])[C:11]=2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 69317962HCID 69317962, compound

Product 1

HCID 69316433HCID 69316433, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 10-(benzyloxy)-2-(4-fluorobenzyl)-8-methyl-1,9-dioxo-1,2,3,4,6,7,8,9-octahydropyrido[3′,4′:4,5]pyrrolo[1,2-a]-pyrazine-4-carboxylate (0.4 g, 0.81 mmol) and manganese(IV) oxide (0.21 g, 2.44 mmol) in toluene (10 mL) was heated in a sealed tube in an oil bath 80° C. overnight. The reaction mixture was cooled to rt, diluted with chloroform (100 mL) and filtered through a pad of Celite. The filtrate was concentrated under vacuum. The filtrate was subjected to column chromatography on silica gel eluting with ethyl acetate. Collection and concentration of appropriate fractions provided the titled compound.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated under vacuum
  4. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-fb7827d97ea2475f979ff56fe63b1888
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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