HCID 66997775, compound → HCID 66996894, compound

HRID 2426475Notes

Reaction equation

HRID 2426475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:34][CH3:35])[C:10](=[O:33])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][CH2:23][O:24]CC4C=CC=CC=4)[C:16](=[O:32])[C:12]3=2)[C:7]1=[O:36].[H][H]>C(OCC)(=O)C.[Rh]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:34][CH3:35])[C:10](=[O:33])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][CH2:23][OH:24])[C:16](=[O:32])[C:12]3=2)[C:7]1=[O:36]

Participants

5

Reactant 2

HCID 66997775HCID 66997775, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66996894HCID 66996894, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 11-(3-chloro-4-fluorobenzyl)-9-methoxy-2-[2-(benzyloxy)ethyl]-3,4,5,6,12,13-hexahydro-2H[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione (0.55 g, 0.97 mmol) and 5% rhodium on carbon (1.10 g) in ethyl acetate (22 mL) was stirred under a balloon of hydrogen at room temperature overnight. The product mixture was filtered through a pad of Celite. The filtrate was concentrated under vacuum to afford the title compound. This material was used in the following reaction without further purification.

Workup

  1. filtrationThe product mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-82c4540805fb4f9284e97f34d3d25ddf
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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