Dichloromethane → Phenylalanine, N-t-butyloxycarbonyl-4-nitro-, t-butyl ester

HRID 1861912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861912
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[C:26](O)([CH3:29])([CH3:28])[CH3:27].Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C>[C:26]([O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)([CH3:29])([CH3:28])[CH3:27]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 1180712-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 546503Phenylalanine, N-t-butyloxycarbonyl-4-nitro-, t-butyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of the compound (6.9 g) obtained in Example 63 and methylene chloride (70 ml) were added t-butanol (20 ml), N,N-dimethylaminopyridine (2.63 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.9 g) and the resulting mixture was stirred at room temperature for 4 days. The reaction mixture was diluted with ethyl acetate and washed successively with 2 N HCl and a saturated aqueous sodium chloride solution; the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 7.64 g of the titled compound (yield, 97%).

Aufarbeitung

  1. washwashed successively with 2 N HCl
  2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-ff96db7c8e374413b724973db09f5f77
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534546B1

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