Sodium Hydroxide → 3(S)-(6-Methoxy-pyridin-3-yl)-3-{2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-imidazolidin-1-yl}-propionic acid

HRID 993248Notes

Reaction equation

HRID 993248 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C@@H:9]([N:14]2[CH:18]=[CH:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[CH2:31][CH2:30][CH2:29][CH2:28][NH:27][C:26]=4[N:32]=3)[C:15]2=[O:33])[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[OH-].[Na+].[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C@@H:9]([N:14]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[CH2:31][CH2:30][CH2:29][CH2:28][NH:27][C:26]=4[N:32]=3)[C:15]2=[O:33])[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 599164503(S)-(6-Methoxy-pyridin-3-yl)-3-[2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-2,3-dihydro-imidazol-1-yl}-propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 102758993(S)-(6-Methoxy-pyridin-3-yl)-3-{2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-imidazolidin-1-yl}-propionic acidYield 87.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-8 (0.40 g, 0.886 mmol), 20% Pd(OH)2 (0.40g), 1N NaOH (2 mL), and ethanol (20 mL) was shaken under 65 psig hydrogen in a Parr apparatus for 18 hours. The mixture was filtered through celite, and the filtrate concentrated. The residue was chromatographed on silica gel (25:10:1:1 to 15:10:1:1 EtOAc/EtOH/NH4OH/H2O) to give 350 mg of 3-9 as a white solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate concentrated
  3. customThe residue was chromatographed on silica gel (25:10:1:1 to 15:10:1:1 EtOAc/EtOH/NH4OH/H2O)

Sources & evidence

ORD record
ord-f3fb1698610d4e86b4a5358c759398da
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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