Hydrochloric Acid → (2S)-2-(((tert-butoxy)carbonyl)amino)-4-cyclohexylbutanoic acid

HRID 383162

반응식

HRID 383162 반응식
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.O1CCOCC1.[OH-].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.[Pt].Cl.C1COCC1.O>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[C:18]([OH:20])=[O:19])=[O:2])([CH3:7])([CH3:5])[CH3:6]

참가 물질

10

반응물 5

HCID 313Hydrochloric Acid2회HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 90495Di-tert-butyl dicarbonateHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

생성물 1

HCID 22862476(2S)-2-(((tert-butoxy)carbonyl)amino)-4-cyclohexylbutanoic acid수율 106%

시약·촉매·용매 4

HCID 150198Platinum hydrochloric acid촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a solution of Boc-homophenylalanine (3.00 g, 10.8 mmol) in CH2Cl2 at room temperature was added a solution of 4N HCl in dioxane (20 mL, 80 mmol), and mixture stirred overnight. Solvents concentrated, and white powder that resulted was reduced under high pressure (4 atm. H2) using platinum/HCl. The white solid that resulted from the reduction was mixed with aqueous 4N NaOH (30 mL), water (30 mL), and THF (50 mL) at room temperature, and to this was added di-t-butyl dicarbonate (3.5 g, 16 mmol). Reaction heated at 70° C. overnight. Reaction cooled to 0° C., and an aqueous solution of 3N HCl added until the pH reached 6. Product extracted out with CHCl3, and extracts dried with Na2SO4, filtered, and concentrated in vacuo to produce a white solid (3.24 g, 106%). m/e (DCI) 286 (MH+)

후처리

  1. concentrationSolvents concentrated
  2. customwhite powder that resulted
  3. customThe white solid that resulted from the reduction
  4. customReaction
  5. customReaction
  6. temperaturecooled to 0° C.
  7. extractionProduct extracted out with CHCl3, and extracts
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9c42513025ff49dba74ab9f6c43a8dd9
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310095B1

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