Hydrochloric Acid → (RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-4-hydroxy-phenyl)-2-ethoxy-acetamide hydrochloride

HRID 1247368Notes

Reaction equation

HRID 1247368 reaction equation
C(OC(=O)[NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21](=[O:35])[CH:22]([C:26]2[C:31]([F:32])=[CH:30][C:29]([OH:33])=[CH:28][C:27]=2[F:34])[O:23][CH2:24][CH3:25])=[CH:15][CH:14]=1)=[NH:12])C1C=CC=CC=1.[ClH:37]>CCO.[Pd]>[ClH:37].[C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][NH:20][C:21](=[O:35])[CH:22]([C:26]2[C:31]([F:32])=[CH:30][C:29]([OH:33])=[CH:28][C:27]=2[F:34])[O:23][CH2:24][CH3:25])=[CH:17][CH:18]=1)(=[NH:10])[NH2:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140474529benzyl N-[4-[[[2-(2,6-difluoro-4-hydroxyphenyl)-2-ethoxyacetyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 21905710(RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-4-hydroxy-phenyl)-2-ethoxy-acetamide hydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

(RS)-[(4-{[2-(2,6-difluoro-4-hydroxy-phenyl)-2-ethoxy-acetylamino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester (100 mg) was dissolved in EtOH (2 ml). 1.25 M HCl in EtOH (0.1 ml) was added and the mixture was hydrogenated 1.5 h at 1 atm H2 in the presence of a catalytic amount of 10% Pd/C. After filtration of the catalyst the solvent was removed to obtain 71 mg (88%) of (RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-4-hydroxy-phenyl)-2-ethoxy-acetamide hydrochloride. White powder. MS 364.3 ([M+H]+).

Workup

  1. filtrationAfter filtration of the catalyst the solvent
  2. customwas removed

Sources & evidence

ORD record
ord-10edcd5089c140adb22f5a59ff4b705d
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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