HCID 69317962, compound → HCID 54692395, compound

HRID 2114852Notes

Reaction equation

HRID 2114852 reaction equation
C([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)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:22]2[CH2:21][CH:20]([C:33]([O:35][CH3:36])=[O:34])[C:11]3[N:12]4[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]4=[C:9]([OH:8])[C:10]=3[C:23]2=[O:24])=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 69317962HCID 69317962, compound

Product 1

HCID 54692395HCID 54692395, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

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 (50 mg, 0.10 mmol) and Pearlman's catalyst (5 mg, 20% Pd(OH)2 on carbon) in ethanol (4 mL) was stirred under an atmosphere of hydrogen gas (1 atm) at room temperature for 1 hr. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under vacuum, and the residue subjected to reverse phase HPLC purification. Collection and lyophilization of appropriate fractions provided the title product.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customphase HPLC purification
  4. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-5698e9a2b5e849dc8a346ceff165446a
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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