4-Pyridinecarboxaldehyde → HCID 18612944, compound

HRID 1420600Notes

Reaction equation

HRID 1420600 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:6]([CH2:11][OH:12])[C:7]([O:9][CH3:10])=[O:8].[N:28]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=1>C(O)C>[N:28]1[CH:33]=[CH:32][C:31]([CH:34]=[N:1][C:2]2[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=2[CH2:4][N:5]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH:6]([CH2:11][OH:12])[C:7]([O:9][CH3:10])=[O:8])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 18612758Methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate

Product 1

HCID 18612944HCID 18612944, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.50 g (1.268 mmol) of methyl 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate and 1.268 mmol of 4-pyridinecarboxaldehyde in 7 ml of anhydrous ethanol was refluxed for 1.5 hours and the mixture concentrated under vacuum to dryness. To the residue was added H2O and ethyl acetate. The ethyl acetate layer was separated and concentrated to dryness under vacuum. The solid was purified by thick layer chromatography on silica gel with hexane-ethyl acetate as solvent to give 0.40 g of solid product (plus a small amount of starting material). Anal. for C24H25N3O6S: Calc'd: C,59.6; H,5.2; N,8.7; Found: C,57.6; H,5.7; N,7.4; Mass spectrum (ES) 484 (M+H)-product; 395.1 (M+H)-starting material.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationthe mixture concentrated under vacuum to dryness
  3. additionTo the residue was added H2O and ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. concentrationconcentrated to dryness under vacuum
  6. customThe solid was purified by thick layer chromatography on silica gel with hexane-ethyl acetate as solvent

Sources & evidence

ORD record
ord-70e83fa32f9a4f0ab6041a2c0146ff06
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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