Ethanol → 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-aminopyridin-4-yl)sulfanyl)propanoate

HRID 2277259Notes

Reaction equation

[C:1]([NH:4][C@@H:5]([CH3:31])[CH2:6][O:7][C:8]1[CH:13]=[C:12]([S:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[O:18])[C:11]([N+:28]([O-])=O)=[CH:10][N:9]=1)(=[O:3])[CH3:2].[Cl-].[NH4+].C(O)C>O>[C:1]([NH:4][C@@H:5]([CH3:31])[CH2:6][O:7][C:8]1[CH:13]=[C:12]([S:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[O:18])[C:11]([NH2:28])=[CH:10][N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-nitropyridin-4-yl)sulfanyl)propanoate (3.38 g), reduced iron (2.07 g), ammonium chloride (0.397 g), ethanol (40 mL) and water (10 mL) was stirred overnight at 80° C. The precipitate was removed by filtration, and the filtrate was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.83 g).

Workup

customThe precipitate was removed by filtration
extractionthe filtrate was extracted with ethyl acetate
washThe combined organic layer were washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-563cde0ddec34020a72f6ebc135f4cc5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133129B2

Reaction notes

Loading…