Lawesson's reagent → HCID 23627814, compound

HRID 1889400Notes

Reaction equation

HRID 1889400 reaction equation
[N:1]#[C:2][C@@H:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:4][C:5](=O)[CH2:6][CH3:7].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:23]2)=CC=1>O1CCCC1>[NH2:1][C:2]1[S:23][C:5]([CH2:6][CH3:7])=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86642155HCID 86642155, compound

Product 1

HCID 23627814HCID 23627814, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 3-nitrilo-N-propionylalaninate (10 g), 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (24.1 g) and tetrahydrofuran (150 mL) was stirred at 70° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. After purification by silica gel column chromatography, the obtained residue was recrystallized from ethyl acetate-hexane to give the title compound as colorless crystals (3.8 g, 38%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe obtained residue was extracted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customAfter purification by silica gel column chromatography
  7. customthe obtained residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a6b1592afe474e15bfd1ac26698566de
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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