Sodium hydride → (Z)-Methyl 2-(benzyloxycarbonylamino)-3-(3-(tert-butoxycarbonyl amino)-6-phenylpyridin-2-yl)acrylate

HRID 2249499

Reaktionsgleichung

Reaktionsgleichung von HRID 2249499
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH:14](P(OCC)(OCC)=O)[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:27]([C:29]1[C:34]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:33][CH:32]=[C:31]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:30]=1)=O>C1COCC1>[CH2:3]([O:10][C:11]([NH:13]/[C:14](=[CH:27]\[C:29]1[C:34]([NH:35][C:36]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:42])=[CH:33][CH:32]=[C:31]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:30]=1)/[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 11068333Methyl 2-(((benzyloxy)carbonyl)amino)-2-(diethyl phosphono)acetateHCID 58670133tert-Butyl 2-formyl-6-phenylpyridin-3-ylcarbamate

Produkt 1

HCID 58670120(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(3-(tert-butoxycarbonyl amino)-6-phenylpyridin-2-yl)acrylateAusbeute 9,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a slurry of 60% of sodium hydride (110 mg, 2.76 mmol) in THF (8 mL) at 0° C. was added 1A (900 mg, 2.5 mmol) in several portions over 10 min. The reaction mixture was then brought to RT for 20 min, then cooled again at 0° C. A suspension of 1E (680 mg, 2.3 mmol) in THF (8 mL) was added over 10 min at 0° C., then the reaction was warmed up to RT. After stirring for 20 min, the reaction was quenched with water (30 mL). The aqueous layer was extracted with EtOAc (50 mL×2). The combined EtOAc extracts were dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as an white foam (105 mg, 9%). LC/MS (method A): retention time=4.16 min, (M+H)+=504.

Aufarbeitung

  1. additionwas added over 10 min at 0° C.
  2. temperaturethe reaction was warmed up to RT
  3. customthe reaction was quenched with water (30 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  5. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel (40 g) column chromatography
  9. washeluting with a gradient of EtOAc (0-60%) in hexane

Quellen und Nachweise

ORD-Eintrag
ord-3c8248fa3e8e4903963be03d2e46aa48
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314882B2

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