Lawesson's reagent → HCID 71254939, compound

HRID 1507630Notes

Reaction equation

HRID 1507630 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([NH:15][C:16](=O)[C:17]([F:20])([F:19])[F:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:32][C:16]([C:17]([F:20])([F:19])[F:18])=[N:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86729692HCID 86729692, compound

Product 1

HCID 71254939HCID 71254939, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-(2,2,2-trifluoroacetamido)propanoate (271 mg, 0.84 mmol) in anhydrous THF (10 mL) was added Lawesson's reagent (682 mg, 1.69 mmol) in one portion and the resulting solution was refluxed for 22 hrs under nitrogen until no starting material is detected by TLC. The solvent was removed under reduced pressure and the crude material was purified by SiO2 chromatography (80% hexanes/20% DCM to 100% DCM in a linear gradient, product elutes in 50% hexanes/50% DCM) (175 mg, 64% yield). 1HNMR (400 MHz, CDCl3): d 7.50 (m, 2H), 7.15 (t, 2H, J=8.8 Hz), 4.31 (q, 2H, J=6.8 Hz), 1.26 (t, 3H, 7.2 Hz).

Workup

  1. temperaturethe resulting solution was refluxed for 22 hrs under nitrogen until no starting material
  2. customThe solvent was removed under reduced pressure
  3. customthe crude material was purified by SiO2 chromatography (80% hexanes/20% DCM to 100% DCM in a linear gradient, product elutes in 50% hexanes/50% DCM) (175 mg, 64% yield)

Sources & evidence

ORD record
ord-5129d3a244f74fdf8b3fa4d4a9f348f9
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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