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Triethylamine → 2-(4-(Tert-butoxycarbonyl)-1-(4,5-dichloro-2-nitrophenyl)piperazin-2-yl)acetic acid

HRID 1896114
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1896114
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[Cl:12].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C)C=O.O>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:5]2[CH:4]=[C:3]([Cl:12])[C:2]([Cl:1])=[CH:7][C:6]=2[N+:8]([O-:10])=[O:9])[CH:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzeneHCID 446077242-(4-(tert-Butoxycarbonyl)piperazin-2-yl)acetic acid

Produkt 1

HCID 672493902-(4-(Tert-butoxycarbonyl)-1-(4,5-dichloro-2-nitrophenyl)piperazin-2-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1,2-Dichloro-4-fluoro-5-nitrobenzene (0.125 mL, 0.952 mmol) and 2-(4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid (256 mg, 1.048 mmol) were dissolved in N,N-dimethylformamide (2 mL) and water (1 mL). Triethylamine (0.398 mL, 2.86 mmol) was slowly added. The resulting mixture was heated at 50° C. overnight. The mixture was concentrated and ethyl acetate was added. 1 N HCl was then added slowly until the pH=6. The water layer was separated and washed multiple times with ethyl acetate. The organic layers were then combined and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 10% to 50% of ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.32 (br, 1 H), 8.17 (s, 1 H), 7.69 (s, 1 H), 3.36-3.90 (m, 4 H), 2.97-3.29 (m, 2 H), 2.88 (dd, J=8.92, 3.37 Hz, 1 H), 2.18-2.47 (m, 2 H), 1.41 (s, 9 H); MS (DCI+) m/z 434.1 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionethyl acetate was added
  3. addition1 N HCl was then added slowly until the pH=6
  4. customThe water layer was separated
  5. washwashed multiple times with ethyl acetate
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with a gradient of 10% to 50% of ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4b42ad2e1a994449a5da30417fb9d65c
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08518933B2

Notizen zur Reaktion

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