Lawesson's reagent → HCID 14371883, compound

HRID 1381963Notes

Reaction equation

HRID 1381963 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:24][CH2:23][C:14]2([C:18](=[O:19])[N:17]([O:20][CH3:21])[C:16](=O)[CH2:15]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:24][CH2:23][C:14]2([C:18](=[O:19])[N:17]([O:20][CH3:21])[C:16](=[S:34])[CH2:15]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14371811HCID 14371811, compound

Product 1

HCID 14371883HCID 14371883, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8-benzyloxycarbonyl-2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione (2.9 g) in toluene (30 ml) was added a Lawesson reagent ([2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphethane-2,4-disulfide]) (2.38 g), and the mixture was heated for 3 hours under reflux. The solvent was then evaporated off under reduced pressure, and the residual oil was dissolved in ethyl acetate (50 ml), which was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated off, and the residual oil was subjected to a silica gel column chromatography [eluent; methanol:dichloromethane=1.50 (V/V)]. The earlier eluate fraction and the later eluate fraction were separated. The solvent for the later eluate fraction was evaporated off and the residual solid was recrystallized from ethyl ether to obtain 2.1 g of a pale yellow solid, m.p. 89° to 90° C.

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. customThe solvent was then evaporated off under reduced pressure
  4. dissolutionthe residual oil was dissolved in ethyl acetate (50 ml)
  5. washwhich was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated off
  8. customThe earlier eluate fraction and the later eluate fraction were separated
  9. customThe solvent for the later eluate fraction was evaporated off
  10. customthe residual solid was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-612f889170d64f37aa359963658e9627
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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