Triethylamine → HCID 57277691, compound

HRID 52851Notes

Reaction equation

HRID 52851 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]([O:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:17])[C@@H:12]([NH2:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[Cl:9].C(N(CC)CC)C.[Si]([O:42][CH:43]1[CH2:49][C:48](=[O:50])[O:47][C:45](=[O:46])[CH2:44]1)(C(C)(C)C)(C)C>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]([O:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:17])[C@@H:12]([NH:14][C:48]([CH2:49][CH:43]([OH:42])[CH2:44][C:45]([OH:47])=[O:46])=[O:50])[CH3:13])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41410403-(tert-Butyldimethylsilyloxy)glutaric anhydrideHCID 70182797(1S,2R)-3-(3,4-dichlorophenyl)-1-methyl-2-(2-naphthoyloxy)propylamine hydrochloride

Product 1

HCID 57277691HCID 57277691, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

129 mg of (1S, 2R)-3-(3,4-dichlorophenyl)-1-methyl-2-(2-naphthoyloxy)propylamine hydrochloride and 120 μl of triethylamine were dissolved in 15 ml of methylene chloride, and 82 mg of 3-(tert-butyldimethylsilyloxy)glutaric anhydride was added thereto with stirring under cooling with ice. The mixture was stirred at room temperature for 3 hours. The reaction solution was extracted by an addition of 1N hydrochloric acid and methylene chloride. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in a liquid mixture of 10 ml of tetrahydrofuran and 5 ml of 1N hydrochloric acid, and the solution was left to stand at room temperature overnight. The reaction solution was extracted by an addition of water and ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent is separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel thin layer chromatography (Kieselgel™ 60F254, Art 5744, manufactured by Merck Co.; chloroform/methanol=6/1) to obtain 112 mg (yield: 71%) of the above-identified compound as white powder.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. extractionThe reaction solution was extracted by an addition of 1N hydrochloric acid and methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe drying agent was separated by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in a liquid mixture of 10 ml of tetrahydrofuran and 5 ml of 1N hydrochloric acid
  8. waitthe solution was left
  9. extractionThe reaction solution was extracted by an addition of water and ethyl acetate
  10. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe drying agent is separated by filtration
  13. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b71c52d3323b4f228fe9750979f11116
Source dataset
uspto-grants-1997_04
Patent number
US05616803

Reaction notes

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