Propylene Glycol → HCID 15679345, compound

HRID 1647385Notes

Reaction equation

HRID 1647385 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:23])[C@H:11]([CH3:22])[NH:12][C:13]([C:15]1[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=1)=[O:14])[CH3:2].C(O)C(O)C.[S:30]([O-])([O-])(=O)=S.[Na+].[Na+]>O>[CH2:1]([O:3][C:4](=[O:24])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:23])[C@H:11]([CH3:22])[NH:12][C:13]([C:15]1[CH:20]=[CH:19][NH:18][C:17](=[S:30])[CH:16]=1)=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 24477Sodium ThiosulfateHCID 15679344HCID 15679344, compound

Product 1

HCID 15679345HCID 15679345, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4.5 g (0.013 mol) of N-[(2-Chloro-4-pyridinyl)carbonyl]-L-alanyl-L-proline ethyl ester (Compound No. 3) in 45 ml of a 10:1 mixture of 1,2-propyleneglycol:water, 15.2 g of sodium thiosulfate are added, and the mixture is heated under reflux for 15 hours. The resulting reaction mixture is diluted with 100 ml of water and extracted with four 100 ml portions of methylene chloride. The organic layer is washed three times with 100 ml of water, dried over anhydrous magnesium sulfate, and the solvent is distilled off at reduced pressure. The residue obtained is purified by crystallisation from a mixture of acetone:petroleum ether, to give the title product as a yellow solid (yield: 85%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 hours
  3. customThe resulting reaction mixture
  4. extractionextracted with four 100 ml portions of methylene chloride
  5. washThe organic layer is washed three times with 100 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off at reduced pressure
  8. customThe residue obtained
  9. customis purified by crystallisation from a mixture of acetone

Sources & evidence

ORD record
ord-7e51fb167ffb4f1d970ef566940d7d99
Source dataset
uspto-grants-1995_07
Patent number
US05432159

Reaction notes

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