HCID 178491485, compound → HCID 21905647, compound

HRID 1247276Notes

Reaction equation

HRID 1247276 reaction equation
O[NH:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11](=[O:24])[CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[OH:23])[O:13][CH3:14])=[CH:7][CH:6]=1)=[NH:4]>C(O)C.C(O)(=O)C.[Pd]>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11](=[O:24])[CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[OH:23])[O:13][CH3:14])=[CH:25][CH:26]=1)(=[NH:2])[NH2:4]

Participants

5

Reactant 1

HCID 178491485HCID 178491485, compound

Product 1

HCID 21905647HCID 21905647, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of (RS)-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-2-(2-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide (240 mg) in ethanol (9 ml) and acetic acid (0.38 ml) was hydrogenated for 7.5 h using 10% Pd/C as a catalyst. The reaction mixture was filtered and the solvent was evaporated. The product was purified by chromatography (silica gel, CH2Cl2=>CH2Cl2/MeOH 4:1) to give (RS)-N-(4-carbamimidoyl-benzyl)-2-(2-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide actetate (12 mg) as an off-white, amorphous solid. MS 344.2 ([M+H]+)

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. customThe product was purified by chromatography (silica gel, CH2Cl2=>CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record
ord-86849e3365284fa9bccfdcf1b144e392
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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