Water → N-piperidinocarbonyl-L-phenylalanine benzyl ester

HRID 1290072Notes

Reaction equation

HRID 1290072 reaction equation
C(N(CC)CC)C.[N:8]1([C:14](Cl)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:17]([O:24][C:25](=[O:35])[C@H:26]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH2:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>ClCCl>[CH2:17]([O:24][C:25](=[O:35])[C@H:26]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH:27][C:14]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 736312Benzyl 3-phenyl-L-alaninate

Product 1

HCID 10595068N-piperidinocarbonyl-L-phenylalanine benzyl esterYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (10.9 g) and piperidinocarbonyl chloride [16 g, see Synthetic Communications, vol. 17, 1887-1892 (1987)] were sequentially added to a solution of L-phenylalanine benzyl ester (39.6 g) in dichloromethane under ice-cooling and the mixture was stirred at room temperature for 24 hours. Water (250 ml) was added to the reaction mixture and the organic layer was separated. The aqueous layer was extracted with dichloromethane (250 ml). The combined organic layer was washed with 0.1N hydrochloric acid (250 ml×2) and a saturated aqueous solution (250 ml) of NaHCO3, and dried over MgSO4. The solvent was distilled away under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 29.3 g of the title compound as white crystals (see Table 8).

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with dichloromethane (250 ml)
  4. washThe combined organic layer was washed with 0.1N hydrochloric acid (250 ml×2)
  5. dry with materiala saturated aqueous solution (250 ml) of NaHCO3, and dried over MgSO4
  6. distillationThe solvent was distilled away under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1681aad81250441d8b3a844023c2e3cb
Source dataset
uspto-grants-1998_05
Patent number
US05750696

Reaction notes

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