4-((2-Fluorophenyl)methoxy)benzaldehyde → Priralfinamide

HRID 2061150Notes

Reaction equation

HRID 2061150 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.Cl.[NH2:19][C@H:20]([C:22]([NH2:24])=[O:23])[CH3:21]>[Pd].[Pt].C(N(CC)CC)C>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:19][C@@H:20]([CH3:21])[C:22]([NH2:24])=[O:23])=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 7027174-((2-Fluorophenyl)methoxy)benzaldehydeHCID 2775816(S)-2-aminopropanamide hydrochloride

Product 1

HCID 5745207PriralfinamideYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 5 g of 4-(2-fluorobenzyloxy)benzaldehyde, prepared according to the Ex. 1 and the corresponding amount L-alaninamide hydrochloride and triethylamine is hydrogenated according to the same procedure of Example 2, but using wet (50% H2O) Pd/C 10% instead of wet (50% H2O) Pt/C 5% to obtain (S)-2-[4-(2-fluorobenzyloxy) benzylamino]propanamide (Ib) in a 70% yield.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-474afb4db86d4088a9a49e2cab40360a
Source dataset
uspto-grants-2012_10
Patent number
US08278485B2

Reaction notes

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