Lawesson's reagent → HCID 59167803, compound

HRID 1039159Notes

Reaction equation

HRID 1039159 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][C:25](=[O:49])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=O)[NH:33][CH2:34][C:35]([C:37]1[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=1[O:44][CH:45]([CH3:47])[CH3:46])=O>C1COCC1>[CH3:23][O:24][C:25](=[O:49])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[S:10][C:35]([C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[O:44][CH:45]([CH3:47])[CH3:46])=[CH:34][N:33]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 591678017-[2-(5-Chloro-2-isopropoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl ester

Product 1

HCID 59167803HCID 59167803, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add Lawesson's reagent (31.03 g, 77 mmol) to a solution of 7-[2-(5-chloro-2-isopropoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl ester (21.80 g, 55 mmol) in THF (550 mL) at room temperature under nitrogen. Heat the mixture at reflux for 3 hours. Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:3), to afford 7-[5-(5-chloro-2-isopropoxyphenyl)thiazol-2-yl]heptanoic acid methyl ester (9.96 g, 46%).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 3 hours
  3. customRemove the solvent under reduced pressure
  4. custompurify the residue by flash column chromatography on silica gel
  5. washeluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-5880e759ecb44faf81737f05c1ef408c
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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