Water → HCID 86620817, Verbindung

HRID 250801

Reaktionsgleichung

Reaktionsgleichung von HRID 250801
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][CH3:5].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1.O.CCOCC>C1C=CC=CC=1>[C:9]1([CH3:19])[CH:10]=[CH:11][C:12]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:13][CH:14]=1.[CH2:19]([O:7][C:6](=[O:8])[C@H:2]([CH2:3][CH2:4][CH3:5])[NH2:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 65098L-Norvaline

Produkt 1

HCID 86620817HCID 86620817, VerbindungAusbeute 180,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A suspension of L-norvaline 1 (1.0 g, 8.53 mmol) benzyl alcohol (5 cm3) and p-toluenesulphonic acid (1.70 g, 8.96 mmol) was heated under reflux in benzene (25 cm3) with the removal of water (Dean-Stark trap) for 17 h (a solution resulted after 5 min). The solution was then cooled to room temperature and dry ether was added. Upon cooling to 0° C. a white solid precipitated and was collected by filtration, washed with dry ether and dried to give p-toluenesulphonate 2 (3.07 g, 95%) as a white solid: mp 142-144° C.; [α]D −1.45 (c 1 in dichloromethane); δH (200 MHz; CDCl3; Me4Si) 0.7 (3H, t, J 7.1, 5-H3), 1.09-1.37, (2H, m, 4-H2), 1.74, (2H, app. quartet, J 7.9, 3-H2), 2.30 (3H, s, Ar—CH3), 3.99 (1H, t, J 6.2, 2-H2), 4.98 (1H, d, J 12.3, OCHAHBPh), 5.11 (1H, d, J 12.3, OCHAHBPh), 7.07 (2H, d, J 8.0, 3′-H); 7.22-7.30 (5H, m, Ph-H) and 7.74 (2H, d, J 8.0, 2′-H); δC (50 MHz; CDCl3) 13.4 (CH3, 5-C), 17.9 (CH2, 4-C), 21.2 (CH3, Ar—CH3) 32.3 (CH2, 3-C), 53.1 (CH, 2-C), 67.6 (CH2, OCH2Ph), 126.0 (CH, Ph), 128.2 (CH, Ph), 128.3 (CH, Ph), 128.4 (CH, Ph), 128.7 (CH, Ph), 134.8 (quat., Ph), 140.2 (quat., Ph), 141.4 (quat., Ph) and 169.4, (quat., 1-C); m/z (FAB) 587.2777[M2.pTsOH.H+: (C12H17NO2)2.C7H8O3S.H requires 587.2791].

Aufarbeitung

  1. temperaturewas heated
  2. customresulted after 5 min)
  3. temperatureUpon cooling to 0° C. a white solid
  4. customprecipitated
  5. filtrationwas collected by filtration
  6. washwashed with dry ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-185decbba7134c8887e13ff5ba9f9e9d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863304B2

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