Benzylamine → Benzyl isovalerate

HRID 843694

Reaktionsgleichung

Reaktionsgleichung von HRID 843694
C(N(CC)CC)C.[CH2:8](N)[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:27]2C=CC=[CH:31][C:26]=2N=N1.[C:43]([O:46]CC)(=[O:45])[CH3:44]>C(Cl)Cl>[CH2:8]([O:46][C:43](=[O:45])[CH2:44][CH:26]([CH3:31])[CH3:27])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 7504BenzylamineHCID 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) (905 mg, 2.08 mmol) in methylene chloride (18 mL) were added sequentially triethylamine (0.72 mL, 5.14 mmol), benzylamine (0.25 mL, 2.29 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (1.01 grams, 2.28 mmol). The mixture was stirred at room temperature overnight and then diluted with ethyl acetate. The solution was washed with 0.5 N hydrochloric acid solution and brine, dried over magnesium sulfate and concentrated under vacuum. The residue was chromatographed on silica gel using a 2:5:16 ratio of methylene chloride/ethyl acetate/hexane affording 2-(R)-2-[benzylcarbamoylmethyl)(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester as a clear oil, 933 mg (86%).

Aufarbeitung

  1. washThe solution was washed with 0.5 N 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 a 2:5:16 ratio of methylene chloride/ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-52a75c38a59a40fb8215132dd525dc6a
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380219B1

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