Hydrochloric Acid → HCID 22397507, Verbindung

HRID 349756

Reaktionsgleichung

Reaktionsgleichung von HRID 349756
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[CH:34]=[C:35]([OH:40])[CH:36]=[CH:37][C:38]=1[F:39].C(OC([N:48]1[CH2:53][CH2:52][CH:51](O)[CH2:50][CH2:49]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[Cl:32][C:33]1[CH:34]=[C:35]([CH:36]=[CH:37][C:38]=1[F:39])[O:40][CH:51]1[CH2:52][CH2:53][NH:48][CH2:49][CH2:50]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 757903-Chloro-4-fluorophenolHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 22397507HCID 22397507, VerbindungAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

DEAD (0.43 ml) was added to a solution of triphenylphosphine (0.72 g), 3-chloro-4-fluorophenol (0.403 g) and 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.5 g) in THF at RT. The resulting mixture was stirred overnight, HCl in dioxan (2 ml of 4M) was added and the mixture stirred at RT overnight. The mixture was then evaporated to dryness and triethylamine (5 ml) was added. The mixture was evaporated and the residue was dissolved in methanol (110 ml), placed onto a SCX cartridge (Varian, 10 g, SCX cartridge available from International Sorbent Technology Isolute® Flash SCX-2) and eluted: first with methanol then with 10% NH3 in methanol. The basic fractions were combined and evaporated to give the product as an oil (0.6 g).

Aufarbeitung

  1. stirringthe mixture stirred at RT overnight
  2. customThe mixture was then evaporated to dryness and triethylamine (5 ml)
  3. additionwas added
  4. customThe mixture was evaporated
  5. dissolutionthe residue was dissolved in methanol (110 ml)
  6. washeluted
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-80db32a74d1f4ba1a5830b7a80dae201
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179922B2

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