Lawesson's reagent → HCID 60054126, compound

HRID 488363Notes

Reaction equation

HRID 488363 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][N:17]([C:22]([O:24][CH3:25])=[O:23])[CH2:16][CH2:15]3)[CH2:7]1)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>C1COCC1>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][N:17]([C:22]([O:24][CH3:25])=[O:23])[CH2:16][CH2:15]3)[CH2:7]1)(=[S:35])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 60054152HCID 60054152, compound

Product 1

HCID 60054126HCID 60054126, compoundYield 134.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 6-[(5S)-5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Example 1, 280 mg, 0.806 mmol) and Lawesson's reagent (179 mg, 0.443 mmol) in dry THF (8.1 mL) under N2 is heated up to 60° C. over 15 mins, stirred at this temperature for 5 mins, and then cooled to ambient temperature and concentrated under reduced pressure. The crude product mixture is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with MeOH/CH2Cl2 (2/98), and those fractions with an Rf=0.57 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated and the residue recrystallized from CH2Cl2/Et2O to give 216 mg (74%) of the title compound as an off-white solid, mp 149-150° C. (dec.); [α]25D=5° (c 0.99, DMSO).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product mixture is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  4. washeluting with MeOH/CH2Cl2 (2/98)
  5. concentrationconcentrated
  6. customthe residue recrystallized from CH2Cl2/Et2O

Sources & evidence

ORD record
ord-a534f5d17aa3479483048218cb2c328e
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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