Pyrrolidine → N-(N-(phenyl)butyryl-L-prolyl)pyrrolidine

HRID 1614595Notes

Reaction equation

HRID 1614595 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl>[CH2:23]1[CH2:24][N:20]([C:14]([C@H:13]2[N:12]([C:10]([CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:11])[CH2:19][CH2:18][CH2:17]2)=[O:16])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 10355295L-Proline, 1-(1-oxo-4-phenylbutyl)-

Product 1

HCID 3081017N-(N-(phenyl)butyryl-L-prolyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

When the reaction was over, the mixture was extracted twice with ethyl ether to remove the unreacted acid chloride. The water phase was acidified by addition of hydrochloric acid. The resulting precipitate was extracted three times with ethyl acetate and the solvent was removed under vacuum, whereby N-(γ-phenyl)butyryl-L-proline was obtained. N-(γ-phenyl)butyryl-L-proline (1 equivalent) was then dissolved in dry methylene chloride (ca. 100 ml) together with pyrrolidine (1 equivalent), WSCD (1 equivalent) was added thereto and the mixture was continuously stirred at room temperature for one whole day and night. After the reaction, the product was washed successively with 1N hydrochloric acid, brine, saturated sodium bicarbonate and brine in that order and was then dried over anhydrous magnesium sulfate. The solvent was distilled off under vacuum and the residue was purified by column chromatography on silica gel, whereby the titled compound was obtained.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. washthe product was washed successively with 1N hydrochloric acid, brine, saturated sodium bicarbonate and brine in that order
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under vacuum
  6. customthe residue was purified by column chromatography on silica gel, whereby the titled compound
  7. customwas obtained

Sources & evidence

ORD record
ord-a19964c57c0e4cb4a03d8dee28633bac
Source dataset
uspto-grants-1993_03
Patent number
US05198458

Reaction notes

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