Triethylamine → 4-Nitrophenyl 3-[4-(2,2-difluoroethyl)phenyl]-5-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate

HRID 220051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220051
[F:1][CH:2]([F:25])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH:14]([C:16]3[O:20][N:19]=[C:18]([CH2:21][CH2:22][O:23][CH3:24])[N:17]=3)[CH2:13][NH:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=1)=[O:35]>ClCCl>[F:25][CH:2]([F:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH:14]([C:16]3[O:20][N:19]=[C:18]([CH2:21][CH2:22][O:23][CH3:24])[N:17]=3)[CH2:13][N:12]([C:34]([O:36][C:37]3[CH:38]=[CH:39][C:40]([N+:43]([O-:45])=[O:44])=[CH:41][CH:42]=3)=[O:35])[CH2:11]2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 596065913-[4-(2,2-Difluoroethyl)phenyl]-5-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]piperidine

Produkt 1

HCID 596065764-Nitrophenyl 3-[4-(2,2-difluoroethyl)phenyl]-5-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 36.3 mg (0.061 mmol, purity 70%) of the compound from Example 61A in dichloromethane (2.0 ml) was admixed with 0.03 ml (21.6 mg, 0.21 mmol) of triethylamine and then 12.3 mg (0.061 mmol) of 4-nitrophenyl chloroformate were added at RT. The mixture was stirred at RT for 2 h and then the reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 56.2 mg (91% of theory, purity 60%)

Aufarbeitung

  1. washthe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-058659f9d3cd4bbe8ac43271d4e80b9d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202862B2

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