HCID 67497636, compound → HCID 136391026, compound

HRID 1628228Notes

Reaction equation

HRID 1628228 reaction equation
[NH2:1][C@@H:2]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:7]=1[O:18]CC1C=CC=CC=1)=[O:4]>CO.[Pd]>[NH2:1][C@@H:2]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:7]=1[OH:18])=[O:4]

Participants

4

Reactant 1

HCID 67497636HCID 67497636, compound

Product 1

HCID 136391026HCID 136391026, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-2-amino-N-(2-(benzyloxy)-5-(pyridin-4-yl)phenyl)-3-phenylpropanamide 13.F (200 mg, 0.473 mmol) in methanol (2 mL) was added 10% Pd on carbon by weight (50 mg). The air was evacuated from the reaction flask and was replaced with hydrogen. The resulting slurry was stirred overnight at room temperature. The reaction mixture was filtered and the mother liquor condensed. The crude material was purified by reverse phase preparative HPLC to afford (S)-2-amino-N-(2-hydroxy-5-(pyridin-4-yl)phenyl)-3-phenylpropanamide 13.G (100 mg, 63% yield).

Workup

  1. customThe air was evacuated from the reaction flask
  2. filtrationThe reaction mixture was filtered
  3. customthe mother liquor condensed
  4. customThe crude material was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-ac00b097e87146daa6d5ed11dc23e48f
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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