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Sodium Carbonate → 3-((R)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one

HRID 525388
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525388
FC(F)(F)S(OC1CC[C@@H](N2C(C3C=CC=CC=3)C(C)(C)OC2=O)CC=1)(=O)=O.FC(F)(F)S(OC1CC[C@H](N2C(C3C=CC=CC=3)C(C)(C)OC2=O)CC=1)(=O)=O.FC1C(C2N=CC=CN=2)=CC(B2OC(C)(C)C(C)(C)O2)=CN=1.C(=O)([O-])[O-].[Na+].[Na+].[F:85][C:86]1[N:91]=[CH:90][C:89]([C:92]2[CH2:97][CH2:96][C@H:95]([N:98]3[CH:102]([C:103]4[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=4)[C:101]([CH3:110])([CH3:109])[O:100][C:99]3=[O:111])[CH2:94][CH:93]=2)=[CH:88][C:87]=1[C:112]1[N:117]=[CH:116][CH:115]=[CH:114][N:113]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:85][C:86]1[N:91]=[CH:90][C:89]([C:92]2[CH2:97][CH2:96][C@@H:95]([N:98]3[CH:102]([C:103]4[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=4)[C:101]([CH3:110])([CH3:109])[O:100][C:99]3=[O:111])[CH2:94][CH:93]=2)=[CH:88][C:87]=1[C:112]1[N:113]=[CH:114][CH:115]=[CH:116][N:117]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 898140903-((S)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-oneHCID 89814340(4R)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonateHCID 898151502-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine2×
HCID 117857261
(4S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate
2×

Produkt 1

HCID 898137833-((R)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-oneAusbeute 47,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A microwave vial was charged with a mixture of (4R)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate and (4S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate (Intermediate M) (730 mg, 1.741 mmol), 2-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine (Intermediate H) (577 mg, 1.915 mmol), sodium carbonate (2 M, 2.611 mL, 5.22 mmol), and tetrakis(triphenylphosphine)palladium(0) (201 mg, 0.174 mmol) (commercially available from Strem Chemicals Inc., Newburyport, Mass.). Dioxane (8.703 mL) was added, the system was purged with argon, and the tube was sealed. The mixture was then stirred at 100° C. in the microwave for 1 hour. LC-MS indicated clean and good conversion to the desired product. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford a yellow oil. The oil was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0 to 60% EtOAc-heptane) to afford a mixture of 3-((S)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one and 3-((R)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (370 mg, 0.832 mmol, 47.8% yield) as a white solid. m/z (ESI) 445.2 (M+H)+.

Aufarbeitung

  1. customthe system was purged with argon
  2. customthe tube was sealed
  3. filtrationThe reaction mixture was filtered through Celite® brand
  4. filtrationfilter aid
  5. concentrationthe filtrate was concentrated
  6. customto afford a yellow oil
  7. customThe oil was purified
  8. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-481dea022a3643a2b5942e5be35dd76c
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340549B2

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