Acetic Acid → (r)-n-(4-Carbamimidoyl-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide acetate

HRID 1247442Notes

Reaction equation

HRID 1247442 reaction equation
C(OC(=O)/[N:10]=[C:11](/[NH2:35])\[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20](=[O:34])[C@H:21]([O:31][CH2:32][CH3:33])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[F:30])=[CH:14][CH:13]=1)C1C=CC=CC=1.[CH3:37][C:38]([OH:40])=[O:39]>CCO.[Pd]>[C:38]([OH:40])(=[O:39])[CH3:37].[C:11]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][NH:19][C:20](=[O:34])[C@H:21]([O:31][CH2:32][CH3:33])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[F:30])=[CH:16][CH:17]=1)(=[NH:10])[NH2:35]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178468204HCID 178468204, compound

Product 1

HCID 69288898(r)-n-(4-Carbamimidoyl-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [1-amino-1-(4-{[(R)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetylamino]-methyl}-phenyl)-meth-(E)-ylidene]-carbamic acid benzyl ester (195 mg) in EtOH (20 ml) was treated with HOAc (0.05 ml) and Pd/C 10% (20 mg) and hydrogenated over night at normal pressure. The catalyst was filtered off, the filtrate was concentrated to give (R)-N-(4-carbamimidoyl-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide acetate (151 mg, 96.3% ee) as white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bce76976fdd84bb2800eaa664ea11b1b
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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