HCID 91215605, compound → HCID 72762834, compound

HRID 1269117Notes

Reaction equation

HRID 1269117 reaction equation
[CH3:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH:23]=[C:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1>CO.[Pd]>[CH3:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1

Participants

4

Reactant 1

HCID 91215605HCID 91215605, compound

Product 1

HCID 72762834HCID 72762834, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-Propyl-2,3,6,7-tetrahydro-1H-azepine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (112.4 mg, 0.212 mmol) in methanol (8.0 mL) was added 10% Pd/C degusa wet form (100 mg). The resulting suspension was hydrogenated at 50 psi for two days. The reaction mixture was filtered through celite, then a 0.45 μm PTFE membrane and evaporation to dryness to furnish the crude product (96 mg, 88%). The crude product was purified by semi-preparative HPLC (Waters Nova-Pak® HR C18, 6 μm particle size, 60 Å pore size, 20 mm ID×100 mm, 5–60% acetonitrile in H2O w/0.1% AcOH over 30 min, 20 mL/min flow rate) to provide the title compound (23.5 mg, 21.5%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customa 0.45 μm PTFE membrane and evaporation to dryness
  3. customto furnish the crude product (96 mg, 88%)
  4. customThe crude product was purified by semi-preparative HPLC (Waters Nova-Pak® HR C18, 6 μm particle size, 60 Å pore size, 20 mm ID×100 mm, 5–60% acetonitrile in H2O w/0.1% AcOH over 30 min, 20 mL/min flow rate)

Sources & evidence

ORD record
ord-df7b6f3c6e1341fb8d674dab66e78ca7
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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