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Thionyl Chloride → HCID 50898388, compound

HRID 1847115
Notes
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Reaction equation

HRID 1847115 reaction equation
O[N:2]=[C:3]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[CH:5]([C:6](=[O:30])[O:7][C:8]3[C@H:9]4[C@:21]([CH3:29])([CH2:22][CH2:23][C:24]=32)[C@@H:12]([C@@H:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:11][CH2:10]4)[CH2:4]1.S(Cl)(Cl)=[O:32].C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH3:28][C@:25]12[CH2:26][CH2:27][NH:2][C:3](=[O:32])[CH2:4][C@@H:5]1[C:6](=[O:30])[O:7][C:8]1[C@@H:9]3[CH2:10][CH2:11][C@H:12]([C@@H:13]([CH2:14][CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[CH3:20])[C@@:21]3([CH3:29])[CH2:22][CH2:23][C:24]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86667487HCID 86667487, compound

Product 1

HCID 50898388HCID 50898388, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 3 (41.5 mg, 0.0999 mmol) obtained in Example 3 was dissolved in 1,4-dioxane (3.0 mL), and thionyl chloride (21.9 μL, 0.300 mmol) was added thereto at room temperature, followed by stirring for 1 hour. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by preparative thin layer chromatography to obtain the title compound (11.6 mg, 28%).

Workup

  1. customat room temperature
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-8b424a794fd34442ace64fb08d4d8c3d
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952003B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes