Ethanol → EtOAc EtOH H2O NH4OH

HRID 322508Notes

Reaction equation

C([C@@:3]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)([CH2:27][C:28]([OH:30])=[O:29])[N:4]([N:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][NH:19][C:18]=3[N:17]=2)[C:9]1=[O:26])[C:5](=[O:7])[CH3:6])C.[OH-:37].[Na+].[CH2:39]([OH:41])[CH3:40]>>[CH3:39][CH2:40][O:30][C:28]([CH3:27])=[O:29].[CH3:6][CH2:5][OH:7].[NH4+:4].[OH-:41].[OH2:37].[O:26]=[C:9]1[N:10]([CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][NH:19][C:18]=3[N:17]=2)[CH2:11][CH2:12][CH2:13][N:8]1[N:4]([C:5](=[O:7])[CH3:6])[C@H:3]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH2:27][C:28]([OH:30])=[O:29]

Participants

Reactant 3

HCID 702Ethanol

HCID 14798Sodium Hydroxide

HCID 86756574Ethyl 2-oxo-3-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)ethyl]-tetrahydropyrimidin-1-yl-acetyl-3(S)-pyridin-3-yl-beta-alanine

Product 2

HCID 86752451EtOAc EtOH H2O NH4OH

HCID 867565732-Oxo-3-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl}ethyl]-tetrahydropyrimidin-1-yl-acetyl-3-(S)-pyridin-3-yl-beta-alanine

Procedure

A mixture of 5-11 (100 mg, 0.22 mmol), 1N NaOH (300 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 5-12 as a white solid. TLC RF=0.22 (silica, 10:10:1:1 EtOAc/ethanol/NH4OH, H2O); 1H NMR (300 MHz, CD3OD) δ 8.66 (m, 1H), 8.39 (m, 1H), 7.95 (m, 1H), 7.53 (d, J=8 Hz, 1H), 7.40 (m, 1H), 6.66 (d, J=8 Hz,1H), 5.1 8 (m, 1H), 4.27 (d, J=7 Hz, 1H), 4.16 (m, 1H), 3.64 (d, J=7 Hz, 1H), 3.50-3.10 (m, 8H), 3.00-2.65 (m, 6H), 1.95 (m, 4H).

Workup

concentrationfollowed by concentration

Sources & evidence

ORD record: ord-ec24b8a5abdb4185b8e254074bead798
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211184B1

Reaction notes

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