Ethanol → EtOAc EtOH H2O NH4OH

HRID 322510Notes

Reaction equation

C([C@@:3]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)([CH2:26][C:27]([OH:29])=[O:28])[N:4]([N:8]1[CH2:12][CH2:11][N:10]([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:9]1=[O:25])[C:5](=[O:7])[CH3:6])C.[OH-:36].[Na+].[CH2:38]([OH:40])[CH3:39]>>[CH3:38][CH2:39][O:29][C:27]([CH3:26])=[O:28].[CH3:6][CH2:5][OH:7].[NH4+:4].[OH-:40].[OH2:36].[O:25]=[C:9]1[N:10]([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)[CH2:11][CH2:12][N:8]1[N:4]([C:5](=[O:7])[CH3:6])[C@H:3]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:26][C:27]([OH:29])=[O:28]

Participants

Reactant 3

HCID 702Ethanol

HCID 14798Sodium Hydroxide

HCID 86754783Ethyl 2-oxo-3-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)ethyl]imidazolidin-1-yl-acetyl-3(S)-pyridin-3-yl-beta-alanine

Product 2

HCID 86752451EtOAc EtOH H2O NH4OH

HCID 867547822-Oxo-3-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl}ethyl]-imidazolidin-1-yl-acetyl-3-(S)-pyridin-3-yl-beta-alanine

Procedure

A mixture of 6-11 (160 mg, 0.33 mmol), 1N NaOH (500 μL), and ethanol (1 mL) was stirred at ambient temperature for 1 hr, followed by concentration. Flash chromatography (silica, 25:10:1:1 to 15:10:1:1 EtOAc/EtOH/NH4OH/H2O) gave 6-12 as a white solid.

Workup

concentrationfollowed by concentration

Sources & evidence

ORD record: ord-be5819c28a52451bb2e5e473c8522c3b
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211184B1

Reaction notes

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