3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[3-(3-[1,8]naphthyridin-2-yl-propyl)-2-oxo-pyrrolidin-1-yl]-propionic acid ethyl ester → 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-pyrrolidin-1-yl)-propionic acid ethyl ester

HRID 1108395Notes

Reaction equation

HRID 1108395 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([C:26]1[CH:34]=[CH:33][C:29]2[CH2:30][CH2:31][O:32][C:28]=2[CH:27]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[C:8]1=[O:25])[CH3:2].[H][H]>CCO.[Pd].[C]>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([C:26]1[CH:34]=[CH:33][C:29]2[CH2:30][CH2:31][O:32][C:28]=2[CH:27]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][NH:18][C:17]=3[N:16]=2)[C:8]1=[O:25])[CH3:2]

Participants

5

Reactant 2

HCID 154537703(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[3-(3-[1,8]naphthyridin-2-yl-propyl)-2-oxo-pyrrolidin-1-yl]-propionic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 154537723(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-pyrrolidin-1-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-3 (460 mg, 1.0 mmol) and 10% Pd/carbon (300 mg) in EtOH (20 mL) was stirred under a balloon of hydrogen for 3 h. Following filtration and evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:25:5 chloroform/ethyl acetate/MeOH) to give 4-4 as a yellow oil.

Workup

  1. filtrationfiltration
  2. customremoval of the solvent
  3. customthe residue was chromatographed (silica gel, 70:25:5 chloroform/ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-1b83c4f0f5f04874b8988cc3d5696795
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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