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Triethylamine → BOC-p-nitrophenylalanine 2-oxopropyl amide

HRID 1762305
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1762305
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:24][CH2:25][C:26](=[O:28])[CH3:27].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(O)(=O)C>[O:28]=[C:26]([CH3:27])[CH2:25][NH:24][C:20](=[O:22])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 30840252-Propanone, 1-amino-, hydrochlorideHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Produkt 1

HCID 18632424
BOC-p-nitrophenylalanine 2-oxopropyl amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

t-Butyloxycarbonyl-p-nitrophenylalanine (4.42 g, 14.26 mmol, aminoacetone hydrochloride (1.56 g, 14.26 mmol), triethylamine (1.44 g, 14.26 mmol), 1-hydroxybenzotriazole (1.69 g, 12.55 mmol), were dissolved in ethyl acetate (400 ml). 1,3-Dicyclohexylcarbodiimide (3.23 g, 15.68 mmol) in ethyl acetate (25 ml) was added and the solution allowed to stir for 18 hours. Glacial acetic acid (0.2 ml) was added and the solution was filtered. The filtrate was extracted with saturated salt solution (100 ml), 1N HCl solution (3×100 ml), saturated salt solution (100 ml), 5% bicarbonate solution (3×100 ml), and saturated salt solution (100 ml). The organic phase was dried over MgSO4, filtered and concentrated to 50 ml. Petroleum ether (50 ml) was added and the solution was cooled to 0° C. for 12 hours. The precipitated product was collected and dried under vacuum.

Aufarbeitung

  1. filtrationthe solution was filtered
  2. extractionThe filtrate was extracted with saturated salt solution (100 ml), 1N HCl solution (3×100 ml), saturated salt solution (100 ml), 5% bicarbonate solution (3×100 ml), and saturated salt solution (100 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to 50 ml
  6. additionPetroleum ether (50 ml) was added
  7. customThe precipitated product was collected
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6aea8be0d8714eafa732cdb6ee1e8460
Quelldatensatz
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04831175

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