Water → N-piperidinocarbonyl-L-phenylalanine benzyl ester

HRID 1290072ノート

反応式

HRID 1290072 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 10595068N-piperidinocarbonyl-L-phenylalanine benzyl ester収率 73.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1681aad81250441d8b3a844023c2e3cb
出典データセット
uspto-grants-1998_05
特許番号
US05750696

反応ノート

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