Pyridine → HCID 854022, compound

HRID 1531802Notes

Reaction equation

HRID 1531802 reaction equation
N1C=CC=CC=1.S(Cl)(Cl)=O.C1C=C2C([N:19]([CH2:22][C:23](O)=[O:24])C(=O)C2=CC=1)=O.[NH:26]1[CH2:33][CH2:32][CH2:31][C@@H:27]1[C:28]([OH:30])=O>ClCCl.O>[C:28]1(=[O:30])[NH:19][CH2:22][C:23](=[O:24])[N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]12

Participants

7

Reactant 4

HCID 1049PyridineHCID 8988D-ProlineHCID 20825N-PhthaloylglycineHCID 24386Thionyl Chloride

Product 1

HCID 854022HCID 854022, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridine (2.5 ml ), and thionyl chloride (22.5 ml) were added to a solution of N-phthaloylglycine (57.5 g) in dichloromethane and the reaction stirred under reflux for 18 hours. The mixture was allowed to cool to room temperature, (R)-proline (30.5 g) added and the reaction again stirred under reflux for 18 hours. On cooling, water was added and the resulting precipitate filtered, washed with further water and dried. This material was suspended in ethanol (330 ml) and dichloromethane (250 ml), and hydrazine hydrate (26.5 ml) added. The reaction mixture was stirred at room temperature for 18 hours, filtered and the filtrate evaporated to dryness in vacuo. This material was crystallised from ethanol, to afford the title compound, 26.05 g.

Workup

  1. temperatureunder reflux for 18 hours
  2. customthe reaction
  3. stirringagain stirred
  4. temperatureunder reflux for 18 hours
  5. temperatureOn cooling
  6. filtrationthe resulting precipitate filtered
  7. washwashed with further water
  8. customdried
  9. additiondichloromethane (250 ml), and hydrazine hydrate (26.5 ml) added
  10. stirringThe reaction mixture was stirred at room temperature for 18 hours
  11. filtrationfiltered
  12. customthe filtrate evaporated to dryness in vacuo
  13. customThis material was crystallised from ethanol

Sources & evidence

ORD record
ord-8ce81e5abd3d4b4e9b827d7570b466c5
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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