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

HRID 2277259
Notes
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Reaction equation

HRID 2277259 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 867313342-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-nitropyridin-4-yl)sulfanyl)propanoate

Product 1

HCID 867313332-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-aminopyridin-4-yl)sulfanyl)propanoateYield 89.6%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

  1. customThe precipitate was removed by filtration
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe combined organic layer were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes