Triethylamine → HCID 10139062, compound

HRID 584977Notes

Reaction equation

HRID 584977 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:3].FC(F)(F)C(O)=O.[CH3:18][NH:19][CH2:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH:34]3[S:38][C:37](=[O:39])[NH:36][C:35]3=[O:40])=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1.C(N(CC)CC)C>ClCCl.O>[O:39]=[C:37]1[NH:36][C:35](=[O:40])[CH:34]([CH2:33][C:30]2[CH:29]=[CH:28][C:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][N:19]([CH3:18])[C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:22]=3)=[CH:32][CH:31]=2)[S:38]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22466Hexyl chloroformateHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 10139062HCID 10139062, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 400 μl (2.5 mmol) of hexyl chloroformate in 5 ml of dichloromethane is added dropwise to a solution of 1 g (2.3 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethyl)-thiazolidine-2,4-dione trifluoroacetate and 1 ml (7.0 mmol) of triethylamine in 15 ml of dichloromethane. The reaction medium is stirred at room temperature for 3 hours, placed in water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (8/2). After evaporation of the solvents, 300 mg (30%) of hexyl N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylcarbamate are obtained in the form of a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (8/2)
  9. customAfter evaporation of the solvents, 300 mg (30%) of hexyl N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylcarbamate
  10. customare obtained in the form of a colorless oil

Sources & evidence

ORD record
ord-b284df13c0c04dc4a75b6d2e01e45d4f
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

Loading…