L-Phenylalanine → HCID 15045083、化合物

HRID 1089855ノート

反応式

HRID 1089855 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][C:16](Cl)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][C:16]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 6140L-PhenylalanineHCID 15045075HCID 15045075、化合物

生成物 1

HCID 15045083HCID 15045083、化合物

試薬・触媒・溶媒 2

HCID 11430Potassium Carbonate溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

3-(Fluoren-9-yl)propionyl chloride (described in Example 33; without crystallization) (3.0 g, 11.7 mmol) in dioxane (40 mL) was added to a stirred solution of L-phenylalanine ((2.0 g, 11.7 mmol) in 75 mL of 10% potassium carbonate solution and 38 mL of dioxane at room temperature. The reaction mixture was stirred overnight. The dioxane was removed under reduced pressure. The residue was diluted with water (100 mL) and extracted with ethyl acetate (4×30 mL). The water solution was treated with Norit then acidified to pH 1. The precipitate was filtered off, washed with 1N HCl, water and dried. Short path chromatography (RP-18 Silica, 50% methanol/water) afforded white solid. Final purification was accomplished by washing the product with ether. The resulting yield of N-[9H-(3-fluoren-9-ylpropionyl)]-L-phenylalanine was 1.2 g 26.5%), mp 194°-195° C.

後処理

  1. customat room temperature
  2. customThe dioxane was removed under reduced pressure
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (4×30 mL)
  5. additionThe water solution was treated with Norit
  6. filtrationThe precipitate was filtered off
  7. washwashed with 1N HCl, water
  8. customdried
  9. customShort path chromatography (RP-18 Silica, 50% methanol/water) afforded white solid
  10. customFinal purification
  11. washby washing the product with ether

出典と根拠

ORDレコード
ord-10006cb8b4b44a7c8b7974f6d52b742f
出典データセット
uspto-grants-1992_01
特許番号
US05079260

反応ノート

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