L-Phenylalanine → HCID 15045083, 화합물

HRID 1089855노트

반응식

HRID 1089855 반응식
[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

참가 물질

5

반응물 2

HCID 6140L-PhenylalanineHCID 15045075HCID 15045075, 화합물

생성물 1

HCID 15045083HCID 15045083, 화합물

시약·촉매·용매 2

HCID 11430Potassium Carbonate용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-10006cb8b4b44a7c8b7974f6d52b742f
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05079260

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