Pyrrolidine → HCID 15598727, compound

HRID 1761518Notes

Reaction equation

HRID 1761518 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:17]([OH:19])=O)[CH:14]([CH3:16])[CH3:15])=[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>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH:14]([CH3:15])[CH3:16])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 15598725HCID 15598725, compound

Product 1

HCID 15598727HCID 15598727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After completion of the reaction, 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-valine was obtained. N-(γ-phenyl)butyryl-L-valine (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 had been washed successively with 1N hydrochloric acid, brine, saturated sodium bicarbonate and brine in that order, and had then been 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 the product
  3. washhad been washed successively with 1N hydrochloric acid, brine, saturated sodium bicarbonate and brine in that order
  4. dry with materialhad then been 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-96a72e869e384b3da829664310a8b0bf
Source dataset
uspto-grants-1989_05
Patent number
US04826870

Reaction notes

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