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Triethylsilane → HCID 56974282, Verbindung

HRID 1417557
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1417557
C([SiH](CC)CC)C.[CH3:8][O:9][C:10]([C@H:12]1[CH2:37][CH2:36][C@:14]2([O:18][CH:17]=[C:16]([C:19]3[CH:24]=[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([F:33])([F:32])[F:31])[CH:22]=[CH:21][C:20]=3[O:34][CH3:35])[CH2:15]2)[C@@H:13]1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)=[O:11]>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10]([C@H:12]1[CH2:37][CH2:36][C@:14]2([O:18][CH2:17][C@H:16]([C:19]3[CH:24]=[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:21][C:20]=3[O:34][CH3:35])[CH2:15]2)[C@@H:13]1[C:38]1[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=1)=[O:11].[CH3:8][O:9][C:10]([C@H:12]1[CH2:37][CH2:36][C@:14]2([O:18][CH2:17][C@@H:16]([C:19]3[CH:24]=[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:21][C:20]=3[O:34][CH3:35])[CH2:15]2)[C@@H:13]1[C:38]1[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=1)=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 12052TriethylsilaneHCID 67670838HCID 67670838, Verbindung

Produkt 2

HCID 56974282HCID 56974282, VerbindungHCID 67670401HCID 67670401, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Triethylsilane (0.0062 mL, 4.5 mg, 0.039 mmol) was added to a solution of (5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]non-2-ene-7-carboxylic acid methyl ester (6.8 mg, 0.013 mmol) in 0.204 mL of trifluoroacetic acid at RT. The mixture was stirred 1 h at RT, then overnight at 60° C. After removing the solvent under reduced pressure, the residue was dissolved in 3.0 mL of ethyl acetate, washed with 2.0 mL of saturated aqueous sodium bicarbonate, dried over sodium sulfate and evaporated. The crude product was purified by preparative TLC, eluting twice with 3% ethyl ether in dichloromethane, to give 1.0 mg of (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester and 2.6 mg of the title compound. 1NMR (400 MHz, CDCl3): δ 7.37 (dd, 2H, J=9, 6 Hz ), 7.19 (d, 1H, J=1 Hz), 7.15 (dd, 1H, J=9, 3 Hz ), 7.09 (d, 1H, J=2 Hz ), 7.08 (d, 1H, J=1 Hz ), 7.03 (t, 2H, J=9 Hz ), 6.82 (1H, J=9 Hz ), 3.78 (s, 3H), 3.70 (t, 1H, J=8 Hz ), 3.62 (t, 1H, J=8 Hz ), 3.56 (s, 3H), 3.14 (ddd, 1H, J=11, 10, 7 Hz ), 3.12 (d, 1H, J=11 Hz ), 2.87 (quintet, 1H, J=8 Hz ), 2.33-2.23 (m, 2H), 2.08-1.88 (m, 4H). Mass spectrum (ESI): m/z=519 (M+1).

Aufarbeitung

  1. customovernight
  2. customat 60° C
  3. customAfter removing the solvent under reduced pressure
  4. dissolutionthe residue was dissolved in 3.0 mL of ethyl acetate
  5. washwashed with 2.0 mL of saturated aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe crude product was purified by preparative TLC
  9. washeluting twice with 3% ethyl ether in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cb7fdc7d2abc400eba347b001ab32efa
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05877191

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