2,4,5-Trichlorophenol → N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl ester

HRID 53085

Reaktionsgleichung

Reaktionsgleichung von HRID 53085
[CH3:1][C:2]([CH3:16])([O:4][C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH3:3].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[O:14][C:13](=[O:15])[C@H:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH:7][C:5]([O:4][C:2]([CH3:3])([CH3:1])[CH3:16])=[O:6]

Komponenten

5

Edukt 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Produkt 1

HCID 15431614N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl esterAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(1,1-Dimethylethoxycarbonyl)leucine (6.32 g, 15 mmol) was stirred with 2,4,5-trichlorophenol (3.01 g, 15.2 mmol) and dicyclohexylcarbodiimide (3.14 g, 15.2 mmol) in ethyl acetate (50 mL) at -10° C. for 4 h. The suspension was filtered and the solvent was evaporated under reduced pressure from the filtrate. The residue was dissolved in ethyl acetate. The suspension was filtered and the solvent was evaporated under reduced pressure from the filtrate to give N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl ester (6.2 g, 99%).

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. customthe solvent was evaporated under reduced pressure from the filtrate
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationThe suspension was filtered
  5. customthe solvent was evaporated under reduced pressure from the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-03579b5b559c4d1b83d5f3479325a6db
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618528

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