Triethylamine → HCID 86594509, compound

HRID 858203Notes

Reaction equation

HRID 858203 reaction equation
O[CH:2]([CH:25]1[S:29][C:28](=[O:30])[NH:27][C:26]1=[O:31])[CH2:3][C@H:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([O:10][CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[O:15][C:16]=2[CH3:17])[CH2:5]1.C(N(CC)CC)C.S(Cl)(C)(=O)=O>ClCCl>[CH3:17][C:16]1[O:15][C:14]([C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[N:13][C:12]=1[CH2:11][O:10][C@@H:6]1[CH2:7][CH2:8][CH2:9][C@H:4]([CH2:3][CH:2]=[C:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])[CH2:5]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 86594508HCID 86594508, compound

Product 1

HCID 86594509HCID 86594509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

344 mg of 5-{1-hydroxy-2-[cis-3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyl]ethyl}thiazolidine-2,4-dione are dissolved in 20 ml of dichloromethane, and 0.13 ml of triethylamine and and 0.12 ml of mesyl chloride are added. The mixture is stirred at room temperature for two hours, and another 0.13 ml of triethylamine and and 0.12 ml of mesyl chloride are added. The mixture is stirred at room temperature for 12 hours. 100 ml of dichloromethane are added, the mixture is washed with saturated sodium bicarbonate solution and dried over magnesium sulfate and the solvent is then removed under reduced pressure. The resulting residue is dissolved in 10 ml of tetrahydrofuran and, at −78° C., 0.22 ml of a 2.7 M solution of n-butyllithium in n-hexane is added. The mixture is stirred at 0° C. for 30 minutes, 20 ml of 1N hydrochloric acid are then added and the mixture is extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 81 mg of 5-{2-[Cis-3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyl]ethylidene}thiazolidine-2,4-dione as a white solid.

Workup

  1. stirringThe mixture is stirred at room temperature for 12 hours
  2. washthe mixture is washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is then removed under reduced pressure
  5. dissolutionThe resulting residue is dissolved in 10 ml of tetrahydrofuran and, at −78° C.
  6. addition0.22 ml of a 2.7 M solution of n-butyllithium in n-hexane is added
  7. stirringThe mixture is stirred at 0° C. for 30 minutes
  8. addition20 ml of 1N hydrochloric acid are then added
  9. extractionthe mixture is extracted three times with in each case 50 ml of ethyl acetate
  10. dry with materialThe combined organic phases are dried over magnesium sulfate
  11. customthe solvent is then removed under reduced pressure
  12. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-a7f4b76e40964d9f99c9764f76c2c46b
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

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