Phenethylamine → Benzyl isovalerate

HRID 343970

Reaktionsgleichung

Reaktionsgleichung von HRID 343970
C(N(CC)CC)C.[CH2:8](CN)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:28]2C=CC=[CH:32][C:27]=2N=N1.[C:44]([O:47]CC)(=[O:46])[CH3:45]>C(Cl)Cl>[CH2:8]([O:47][C:44](=[O:46])[CH2:45][CH:27]([CH3:32])[CH3:28])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Produkt 1

HCID 7651Benzyl isovalerate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(R)-2-[carboxymethyl(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester (Example 1) (1.05 grams, 2.41 mmol) in methylene chloride (20 mL) were added sequentially triethylamine (0.84 mL, 6.0 mmol),N-benzylmethylamine (0.34 mL, 2.63 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (1.17 grams, 2.69 mmol). The mixture was stirred at room temperature overnight and then diluted with ethyl acetate. The solution was washed with 0.5N hydrochloric acid solution and brine, dried over magnesium sulfate and concentrated under vacuum. The residue was chromatographed on silica gel using 35% ethyl acetate in hexane (plus a small amount of methylene chloride to load the sample on the column) affording 2-(R)-2-[benzylmethylcarbamoylmethyl)(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester as a clear oil, 1.14 grams (88%).

Aufarbeitung

  1. washThe solution was washed with 0.5N hydrochloric acid solution and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was chromatographed on silica gel using 35% ethyl acetate in hexane (plus a small amount of methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-1c301499333d4c0b96ddb53ab9809753
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05863949

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