Sodium Hydroxide → (2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-pyridin-3-yl-beta-alanine

HRID 322506Notes

Reaction equation

HRID 322506 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[NH:7][C:8](=[O:28])[CH2:9][N:10]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[CH2:23][CH2:22][CH2:21][NH:20][C:19]=3[N:18]=2)[C:11]1=[O:27])[CH3:2].[OH-:36].[Na+]>C(O)C>[CH3:2][CH2:1][O:3][C:4]([CH3:5])=[O:35].[CH3:2][CH2:1][OH:3].[NH4+:7].[OH-:36].[OH2:3].[O:27]=[C:11]1[CH:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[CH2:23][CH2:22][CH2:21][NH:20][C:19]=3[N:18]=2)[CH2:13][CH2:14][N:10]1[CH2:9][C:8]([NH:7][C@H:6]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[CH2:5][C:4]([OH:35])=[O:3])=[O:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86754780(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-pyridin-3-yl-beta-alanine ethyl ester

Product 2

HCID 44368757(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-pyridin-3-yl-beta-alanineHCID 86752451EtOAc EtOH H2O NH4OH

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-12 (0.1 g, 0.15 mmol), 1N NaOH (300 μL) and ethanol (1 mL) was stirred at ambient temperature for 1 hr. Concentration and the flash chromatography (silica, 25:10:1:1→15:10:1:1 EtOAc/EtOH/NH4OH/H2O) gave 2-14 as a white solid.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-4627002f9a8e4825846b426721e3f7f3
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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