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Iodine → HCID 59909851, Verbindung

HRID 2183031
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2183031
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[CH:29]1([CH2:35][CH2:36][CH2:37][C@@H:38]([C:47]([NH:49][CH:50]([C:54]([O:56][CH3:57])=[O:55])[C:51](=[O:53])[CH3:52])=O)[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O1CCCC1.O>[C:43]([O:42][C:40](=[O:41])[CH2:39][C@H:38]([C:47]1[O:53][C:51]([CH3:52])=[C:50]([C:54]([O:56][CH3:57])=[O:55])[N:49]=1)[CH2:37][CH2:36][CH2:35][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)([CH3:44])([CH3:46])[CH3:45]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59909746HCID 59909746, Verbindung

Produkt 1

HCID 59909851HCID 59909851, VerbindungAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A suspension of triphenylphosphine (9.49 g, 36.18 mmol), iodine (7.98 g, 31.44 mmol) and triethylamine (8.49 ml, 60.75 mmol) in tetrahydrofuran was cooled to −78° C. then treated with tert-butyl (3R)-6-cyclohexyl-3-({[1-(methoxycarbonyl)-2-oxopropyl]amino}carbonyl)hexanoate (Preparation 68) (4.86 g, 11.80 mmol) over 15 minutes. The mixture was stirred at −78° C. for 30 minutes then at 0-5° C. for 2 hours. The mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (0:100 to 10:90) to afford the title compound as a colourless oil (2.92 g).

Aufarbeitung

  1. waitat 0-5° C. for 2 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (0:100 to 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-e3977aefc3104ac48d5042bc1b54308e
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06897306B2

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