N-Hydroxysuccinimide → HCID 15231858, compound

HRID 1110012Notes

Reaction equation

HRID 1110012 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[C:12]([OH:22])[C:13]([C:19]([OH:21])=O)=[CH:14]2.ON1C(=O)CCC1=O.[NH2:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH:37]([O:40][CH:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:36][CH2:35]1>ClCCl>[CH:41]([O:40][CH:37]1[CH2:38][CH2:39][N:34]([CH2:33][CH2:32][NH:31][C:19]([C:13]2[C:12]([OH:22])=[CH:11][C:10]3[C:15](=[CH:16][CH:17]=[CH:18][C:9]=3[O:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:14]=2)=[O:21])[CH2:35][CH2:36]1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 11130710HCID 11130710, compoundHCID 19018666HCID 19018666, compound

Product 1

HCID 15231858HCID 15231858, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

591 mg (2.0 mM) of 5-(2-pyridylmethoxy)3-hydroxy-2-naphthoic acid was dissolved in 20 ml of dichloromethane. Thereto were added 235 mg (2.0 mM) of N-hydroxysuccinimide and 422 mg (2.0 mM) of dicyclocarbodiimide. The resulting mixture was stirred at room temperature for 1 hour. Thereto was dropwise added a solution of 620 mg (2.0 mM) of 1-(2-aminoethyl)-4-(benzhydryloxy)-piperidine in 20 ml of dichloromethane. Stirring was conducted at room temperature for 2 hours to give rise to a reaction. After the completion of the reaction, extraction with dichloromethane was conducted. The extract was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution two times, and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was mixed with 20 ml of acetonitrile. The mixture was filtered, and the filtrate was subjected to distillation to remove the solvent. The residue was purified by silica gel chromatography to obtain 632 mg of the title compound at a yield of 67%.

Workup

  1. stirringStirring
  2. waitwas conducted at room temperature for 2 hours
  3. customto give rise
  4. customto a reaction
  5. washThe extract was washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materiala saturated aqueous sodium chloride solution two times, and dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation
  8. additionThe residue was mixed with 20 ml of acetonitrile
  9. filtrationThe mixture was filtered
  10. distillationthe filtrate was subjected to distillation
  11. customto remove the solvent
  12. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4d867e811f824e4e948eaea6c69cd6e9
Source dataset
uspto-grants-1994_06
Patent number
US05324728

Reaction notes

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