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Triethylamine → HCID 178471797, Verbindung

HRID 505312
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505312
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]1)[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:22][C:23]1[CH:50]=[CH:49][C:48]([O:51][C:52]([F:55])([F:54])[F:53])=[CH:47][C:24]=1[CH2:25][N:26]1[C@@H:30]([CH3:31])[C@@H:29]([C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=2)[O:28][C:27]1=[O:46].C(N(CC)CC)C>C1COCC1.CN(C=O)C>[F:45][C:42]([F:43])([F:44])[C:34]1[CH:33]=[C:32]([C@H:29]2[O:28][C:27](=[O:46])[N:26]([CH2:25][C:24]3[CH:47]=[C:48]([O:51][C:52]([F:53])([F:54])[F:55])[CH:49]=[CH:50][C:23]=3[NH:22][C:12]([C@H:9]3[CH2:8][CH2:7][C@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH2:11][CH2:10]3)=[O:14])[C@H:30]2[CH3:31])[CH:37]=[C:36]([C:38]([F:39])([F:41])[F:40])[CH:35]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57617867(4S,5R)-3-[2-amino-5-(trifluoromethoxy)benzyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-oneHCID 178471800HCID 178471800, Verbindung

Produkt 1

HCID 178471797HCID 178471797, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of trans-4-(2-ethoxy-2-oxoethyl)-cyclohexanecarboxylic acid (1 g; 4.67 mmol) in anhydrous THF (25 mL) at 0° C. was treated dropwise with oxalyl chloride (1.02 mL; 11.68 mmol) followed by catalytic DMF (50 μL). The reaction was stirred at room temperature for 2 h, concentrated in vacuo, and the residue was redissolved in THF (25 mL). The resultant solution was cooled to 0° C. and treated with (4S,5R)-3-[2-amino-5-(trifluoromethoxy)benzyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (2.58 g; 5.14 mmol) and triethylamine (0.716 mL; 5.14 mmol). The reaction was stirred at room temperature for 1 h, quenched with water and partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous layer was extracted with EtOAc (3×100 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography, eluting with EtOAc/hexanes, to afford ethyl [trans-4-({[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl]amino}carbonyl)cyclohexyl]acetate as an off-white solid. LCMS=698.9 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 8.94 (s, 1 H), 8.23 (d, J=8.9 Hz, 1 H), 7.92 (s, 1 H), 7.73 (s, 2H), 7.27-7.24 (m, 1 H), 7.02 (s, 1 H), 5.71 (d, J=8.4 Hz, 1 H), 4.78 (d, J=15.5 Hz, 1 H), 4.19-4.12 (m, 3H), 4.07 (d, J=15.6 Hz, 1 H), 2.43-2.37 (m, 1 H), 2.21 (d, J=6.9 Hz, 2 H), 2.07-1.98 (m, 2 H), 1.93-1.83 (m, 3 H), 1.67 (q, J=12.6 Hz, 2 H), 1.26 (t, J=7.2 Hz, 3 H), 1.19-1.11 (m, 2 H), 0.88 (d, J=6.6 Hz, 3 H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was redissolved in THF (25 mL)
  3. temperatureThe resultant solution was cooled to 0° C.
  4. stirringThe reaction was stirred at room temperature for 1 h
  5. customquenched with water
  6. custompartitioned between EtOAc (100 mL) and H2O (100 mL)
  7. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  8. washthe combined extracts were washed with brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash silica gel chromatography
  13. washeluting with EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4cc2b7b07606497b951580fb536078ba
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781426B2

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