Pyridine → HCID 18612947, compound

HRID 1264585Notes

Reaction equation

HRID 1264585 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]([CH2:10]O)[C:7]([O-:9])=[O:8].[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].N1C=CC=C[CH:39]=1>>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:5]2[CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[N:1]([S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:10][CH:6]2[C:7]([O:9][CH3:39])=[O:8])(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 18613031HCID 18613031, compound

Product 1

HCID 18612947HCID 18612947, compound

Conditions

Temperature
0 °C

Procedure

To 0.50 g (1.26 mmol) of 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate in 5 ml of pyridine cooled to 0° C. was added 0.284 g (2.59 mmol) of tosyl chloride. The mixture was stirred at 0° C. for 2 hours and then concentrated to remove the solvent. To the residue was added 8 ml of anhydrous ethanol and the mixture refluxed for 2 days. The mixture was concentrated to dryness and ethyl acetate added. The mixture was washed with H2O, 2 N citric acid, brine and dried with Na2SO4. The filtrate was filtered through a thin pad of hydrous magnesium silicate and the filter pad washed with ethyl acetate. The filtrate was concentrated to dryness to give 0.60 g of a foam. Anal. for C25H26N2O7S2: Calc'd: C, 56.6; H, 4.9; N, 5.3; S, 12.1; Found: C, 56.2; H, 5.2; N, 5.2; S, 11.4.

Workup

  1. concentrationconcentrated
  2. customto remove the solvent
  3. additionTo the residue was added 8 ml of anhydrous ethanol
  4. temperaturethe mixture refluxed for 2 days
  5. concentrationThe mixture was concentrated to dryness and ethyl acetate
  6. additionadded
  7. washThe mixture was washed with H2O, 2 N citric acid, brine
  8. dry with materialdried with Na2SO4
  9. filtrationThe filtrate was filtered through a thin pad of hydrous magnesium silicate
  10. washthe filter pad washed with ethyl acetate
  11. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-947ea12a2976438f922412c93b91df77
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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