Lawesson's reagent → HCID 86602461, compound

HRID 1160323Notes

Reaction equation

HRID 1160323 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:27][C:28](=[O:58])[CH2:29][CH:30]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:43]=[C:44]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)[CH:45]=[CH:46][CH:47]=2)=[CH:36][CH:35]=1)[C:31]([NH2:33])=O)([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([O:27][C:28](=[O:58])[CH2:29][CH:30]([C:31](=[S:10])[NH2:33])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:43]=[C:44]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)[CH:45]=[CH:46][CH:47]=2)=[CH:36][CH:35]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68674801HCID 68674801, compound

Product 1

HCID 86602461HCID 86602461, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawesson's reagent (81 mg, 0.2 mmol) was added to a solution of compound 51.1 (50 mg, 0.1 mmol) in THF (2 mL). The resulting mixture was stirred at room temperature for 6 h. The reaction was quenched with water (5 mL). The reaction mixture was extracted with dichloromethane (3 mL×3). The organic extracts were combined, dried over MgSO4 and concentrated under reduced pressure. The product was purified via flash chromatography (50% ethyl acetate in hexanes) to yield compound 51.2 (40 mg) as a clear film. MS ESI (pos.) m/e: 516 (M+H). 1H NMR (400 MHz) (CDCl3) δ 7.72 (4H, s); 7.67 (1H, s); 7.51-7.48 (3H, m); 7.31-7.28 (2H, m); 7.0-6.97 (2H, m); 5.14 (2H, s); 4.25-4.22 (1H, m); 3.51-3.46 (1H, m); 2.78-2.72 (1H, m); 1.38 (9H, s).

Workup

  1. customThe reaction was quenched with water (5 mL)
  2. extractionThe reaction mixture was extracted with dichloromethane (3 mL×3)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified via flash chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-57b1b87dc905438da4356931cb7e5fde
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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