Water → HCID 87301721, compound

HRID 885958Notes

Reaction equation

HRID 885958 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[C:10](=O)[NH:11][CH2:12][CH2:13][C:14]=3[N:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1.C(Cl)Cl.O>C1COCC1>[N:1]1([C:7]2[S:8][C:9]3[C:10](=[S:26])[NH:11][CH2:12][CH2:13][C:14]=3[N:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 87949Lawesson's reagentHCID 67186754HCID 67186754, compound

Product 1

HCID 87301721HCID 87301721, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 3 (0.139 g, 0.58 mmol) in THF (10 mL) was added Lawesson's reagent (2.36 g, 5.8 mmol). The suspension was stirred for 1 week. DCM (10 mL) and water (10 mL) were added. The aqueous fraction was extracted with DCM (3×15 mL). The combined organic fractions were washed with water (3×20 mL), dried (MgSO4), filtered and the solvent evaporated in vacuo. The oily residue was purified by column chromatography (SiO2, 1:1 EtOAc/hexanes). Fractions containing the title compound were concentrated and the residue washed with Et2O to give the title compound (0.088 g, 51%) as a yellow solid. δH (DMSO-d6) 9.38 (1H, s), 3.69 (4H, t, J 4.8 Hz), 3.51 (4H, t, J 4.8 Hz), 3.44-3.48 (2H, m), 2.74 (2H, t, J 7.6 Hz). LCMS (ES+), 256.0 (M+H)+, RT 2.60 minutes (Method 5).

Workup

  1. extractionThe aqueous fraction was extracted with DCM (3×15 mL)
  2. washThe combined organic fractions were washed with water (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe oily residue was purified by column chromatography (SiO2, 1:1 EtOAc/hexanes)
  7. additionFractions containing the title compound
  8. concentrationwere concentrated
  9. washthe residue washed with Et2O

Sources & evidence

ORD record
ord-dc22a5cc03f44169b8142a1c791b46d2
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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