Ethanol → HCID 10117272, compound

HRID 900753Notes

Reaction equation

HRID 900753 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:34])=[C:5]([CH2:11][C:12]2[S:27][C:15]3[N:16]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:17](=[O:22])[N:18]([CH3:21])[C:19](=[O:20])[C:14]=3[C:13]=2[C:28]([N:30]([O:32][CH3:33])[CH3:31])=[O:29])[C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH2:35](O)C>[Pd]>[C:7]([O:9][CH2:10][CH3:35])(=[O:8])[CH3:6].[CH3:34][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:2].[CH3:34][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:2].[CH3:35][C:28]([CH3:13])=[O:29].[CH3:1][C:2]1[NH:3][C:4]([CH3:34])=[C:5]([CH2:11][C:12]2[S:27][C:15]3[N:16]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:17](=[O:22])[N:18]([CH3:21])[C:19](=[O:20])[C:14]=3[C:13]=2[C:28]([N:30]([O:32][CH3:33])[CH3:31])=[O:29])[C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 2

HCID 702Ethanol2×HCID 10117272HCID 10117272, compound

Product 3

HCID 10117272HCID 10117272, compoundHCID 21882781Isohexane ethyl acetateHCID 87088216HCID 87088216, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The product of step c) (189 mg) in dry ethanol (18 ml) was treated with a slurry of 10% Pd/C (20 mg) in dry ethanol (2 ml) and hydrogenated at 4 bar for 75 min. Filtration from catalyst and evaporation gave a residue which was purified by chromatography in two stages: firstly (SiO2/3:1 ethyl acetate-isohexane) and secondly (SiO2/2:1 isohexane-acetone) to afford the title compound (85 mg).

Workup

  1. filtrationFiltration
  2. customfrom catalyst and evaporation
  3. customgave a residue which
  4. customwas purified by chromatography in two stages

Sources & evidence

ORD record
ord-be24e0b9b0964b9294eed4db58a2413c
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

Loading…