Triethylamine → (2R*,4S*)-2-benzyl-1-(3,5-bis-(trifluoromethyl)-benzoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

HRID 1033302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033302
O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[CH2:23]([C@@H:30]1[CH2:35][C@@H:34]([N:36]([CH2:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]=[CH:46][CH:45]=2)[C:37](=[O:42])[C:38]([F:41])([F:40])[F:39])[CH2:33][CH2:32][NH:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[F:54][C:55]([F:70])([F:69])[C:56]1[CH:57]=[C:58]([CH:62]=[C:63]([C:65]([F:68])([F:67])[F:66])[CH:64]=1)[C:59](O)=[O:60]>C(Cl)Cl>[CH2:23]([C@@H:30]1[CH2:35][C@@H:34]([N:36]([CH2:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]=[CH:46][CH:45]=2)[C:37](=[O:42])[C:38]([F:40])([F:41])[F:39])[CH2:33][CH2:32][N:31]1[C:59](=[O:60])[C:58]1[CH:62]=[C:63]([C:65]([F:66])([F:67])[F:68])[CH:64]=[C:56]([C:55]([F:54])([F:69])[F:70])[CH:57]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Produkt 1

HCID 57101830(2R*,4S*)-2-benzyl-1-(3,5-bis-(trifluoromethyl)-benzoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

143 mg (561 mmol) of bis-(2-oxo-3-oxazolidinyl)phosphinic chloride and 144 μl (1.03 mmol) of triethylamine are added to a solution of 200 mg (467 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine and 113 mg (561 mmol) of 3,5-bis-(trifluoromethyl)-benzoic acid in 3 ml of methylene chloride, and the reaction mixture is left to stir at room temperature for 16 hours. It is then diluted with methylene chloride, and the organic phase is washed once each with 10% strength citric acid, 1N sodium bicarbonate solution and with brine, dried over magnesium sulfate and evaporated to dryness. The yellowish foam is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (1000:50:1). The title compound is obtained as yellow oil. TLC: methylene chloride/methanol/conc. ammonia (1000: 50:1) Rf =0.34, FD-MS: M+ =667.

Aufarbeitung

  1. waitthe reaction mixture is left
  2. washthe organic phase is washed once each with 10% strength citric acid, 1N sodium bicarbonate solution
  3. dry with materialwith brine, dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe yellowish foam is chromatographed on silica gel with methylene chloride/methanol/conc

Quellen und Nachweise

ORD-Eintrag
ord-9efcf4467a224d228a1ea2328c9baa92
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310743

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