Sodium Hydroxide → EtOAc EtOH H2O NH4OH

HRID 322505Notes

Reaction equation

HRID 322505 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C@@H:6]([C:29]#[CH:30])[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-:32].[Na+]>C(O)C>[CH3:2][CH2:1][O:3][C:4]([CH3:5])=[O:31].[CH3:2][CH2:1][OH:3].[NH4+:7].[OH-:32].[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]#[CH:30])[CH2:5][C:4]([OH:31])=[O:3])=[O:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86754778(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-ethynyl-beta-alanine ethyl ester

Product 2

HCID 86752451EtOAc EtOH H2O NH4OHHCID 86754779(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-ethynyl-beta-alanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-11 (0.1 g, 0.15 mmol), 1N NaOH (300 μL, and ethanol (1 mL) was stirred at ambient temperature for 1 hr. Concentration and then flash chromagraphy (silica, 25:10:1:1→15:10:1:1 EtOAc/EtOH/NH4OH/H2O) gave 2-13 as a white solid.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-683b4928bb5d4e8fa7539d8d9774246f
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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