Ethanol → EtOAc EtOH H2O NH4OH

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Ethyl 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	HCID 86756574	—
Product	EtOAc EtOH H2O NH4OH	HCID 86752451	—
Product	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	HCID 86756573	—

Reaction Steps

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).

Provenance & Evidence

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