Sodium Iodide → (3S)-N-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-L-phenylalanyl]-L-leucine, t-butyl ester

HRID 652358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652358
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:26]C(CCl)=O.[C:31]([O:35][C:36]([NH:38][C@H:39]([C:47]([OH:49])=O)[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:37])([CH3:34])([CH3:33])[CH3:32].C(=O)(O)[O-].[Na+].[I-].[Na+]>CN(C)C=O>[C:31]([O:35][C:36]([NH:38][C@@H:39]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:47](=[O:49])[CH2:26][NH:1][C@H:2]([C:10]([NH:12][C@H:13]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:37])([CH3:32])([CH3:33])[CH3:34]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 6352601H-Phe-Leu-OButHCID 88667995N-[(t-Butyloxy)carbonyl]-L-phenylalanine chloromethyl ketone

Produkt 1

HCID 131714427(3S)-N-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-L-phenylalanyl]-L-leucine, t-butyl esterAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of L-phenylalanyl-L-leucine, t-butyl ester (4.13 g, 12 mmol) in 60 ml of dimethylformamide under argon was added N-[(t-butyloxy)carbonyl]-L-phenylalanine chloromethyl ketone (3.57 g, 12 mmol, see example 4A), sodium bicarbonate (1.01 g, 12 mmol) and sodium iodide (900 mg, 6 mmol, 0.5 equiv.). The reaction mixture was allowed to stir overnight, then the solvent was evaporated (<25° C., vacuum pump). The residue was taken up into ethyl acetate (300 ml) and washed with water (3×40 ml) and brine (40 ml), then dried (sodium sulfate) and evaporated to give 6.63 g of a yellow oil. This oil was purified by flash chromatography on 450 g of Merck silica gel (230-400 mesh), eluting with 3:1 hexane-ethyl acetate, to yield 5.05 g of the title compound as a light yellow solid. A portion was recrystallized from ethyl acetate-hexane to give a white solid, melting point 85°-87° C.

Aufarbeitung

  1. customthe solvent was evaporated (<25° C., vacuum pump)
  2. washwashed with water (3×40 ml) and brine (40 ml)
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-309386c5036c4327b57186ba0aa50a49
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670541

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