Sodium hydride → 3-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

HRID 604647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604647
[H-].[Na+].[F:3][C:4]([F:23])([F:22])[C:5]1[CH:6]=[C:7]([C@H:15]2[O:19][C:18](=[O:20])[NH:17][C@H:16]2[CH3:21])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.[F:24][C:25]([F:43])([F:42])[S:26]([O:29][C:30]1[C:39]([CH2:40]Br)=[CH:38][C:37]2[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=2[CH:31]=1)(=[O:28])=[O:27].[NH4+].[Cl-]>C1COCC1>[F:42][C:25]([F:24])([F:43])[S:26]([O:29][C:30]1[C:39]([CH2:40][N:17]2[C@@H:16]([CH3:21])[C@@H:15]([C:7]3[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:5]([C:4]([F:3])([F:22])[F:23])[CH:6]=3)[O:19][C:18]2=[O:20])=[CH:38][C:37]2[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=2[CH:31]=1)(=[O:27])=[O:28]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-oneHCID 575763013-(Bromomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Produkt 1

HCID 866276293-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (6-8 mg, 60% dispersion in mineral oil, 0.205 mmol) was added to a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (49.0 mg, 0.156 mmol) in dry THF (2 mL) at room temperature under N2. After stirring for 15 min at room temperature a solution of 3-(bromomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (48.6 mg, 0.130 mmol) in dry THF (3 mL) was added via cannula. The reaction mixture was stirred for 4 h at room temperature. Saturated NH4Cl (10 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient) to afford 3-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate, as a colorless oil. Rf=0.51 (20% EtOAc/hexanes). LCMS calc.=606.1; found 606.2 (M+1)+. 1H NMR (500 MHz, CDCl3): δ 7.88 (s, 1H); 7.76 (s, 2H); 7.20 (s, 1H); 6.99 (s, 1H); 5.69 (d, J=7.9 Hz, 1H); 4.80 (d, J=15.6 Hz, 1H); 4.25 (d, J=15.6 Hz, 1H); 4.08-4.02 (m, 1H); 2.81-2.74 (m, 4H); 1.82-1.80 (m, 4H); 0.77 (d, J=6.5 Hz, 3H).

Aufarbeitung

  1. additionwas added via cannula
  2. extractionthe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThis was purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-cc9a9fd1e03a45c1a986b76ec689a1ad
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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