Lawesson's reagent → HCID 86590643, compound

HRID 722002Notes

Reaction equation

HRID 722002 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:26][CH2:27][C@@:28]1([CH3:50])[O:32][C@@H:31]([N:33]2[CH:41]=[C:39]([CH3:40])[C:37](=O)[NH:36][C:34]2=[O:35])[C@H:30]([O:42][C:43](=[O:45])[CH3:44])[C@@H:29]1[O:46][C:47](=[O:49])[CH3:48])(=[O:25])[CH3:24]>ClCCCl>[C:23]([O:26][CH2:27][C@@:28]1([CH3:50])[O:32][C@@H:31]([N:33]2[CH:41]=[C:39]([CH3:40])[C:37](=[S:10])[NH:36][C:34]2=[O:35])[C@H:30]([O:42][C:43](=[O:45])[CH3:44])[C@@H:29]1[O:46][C:47](=[O:49])[CH3:48])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 69484646HCID 69484646, compound

Product 1

HCID 86590643HCID 86590643, compoundYield 137.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Lawesson's reagent (119 mg, 0.29 mmol) was added under argon to a solution of 15 (0.167 g, 4.19 mmol) in anhydrous 1,2-dichloroethane (11 mL) and the reaction mixture was stirred overnight under reflux. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (1–2%) in chloroform] to give pure 16 (0.165 g, 95%) as a yellow foam. 1H-NMR (DMSO-d6): δ 12.81 (s, 1H, NH), 7.64 (s, 1H, H-6), 5.84 (d, 1H, H-1′, J1′-2′=4.66 Hz), 5.5–5.4 (m, 2H, H-2′ and H-3′), 4.11 (dd, 2H, H-5′ and H-5″, J=11.7 Hz, J=31.3 Hz), 2.0–1.8 (m, 12H, 3 CH3CO2 and CH3), 1.33 (s, 3H, CH3); MS (matrix GT): FAB>0 m/z 829 (2M+H)+, 415 (M+H)+, 273 (S)+, 143 (BH2)+, 43 (CH3CO)+ FAB<0 m/z 827 (2M−H)−, 413 (M−H)−, 141 (B)31 , 59 (CH3CO2)−.

Workup

  1. temperatureunder reflux
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-ce89a41f9d6a46a39dd3acc1135da703
Source dataset
uspto-grants-2006_11
Patent number
US07138376B2

Reaction notes

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