Nitrogen → (S)-methyl 4-(1,3-dioxoisoindolin-2-yloxy)-2-methoxybutanoate

HRID 656586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656586
[OH:1][CH2:2][CH2:3][C@H:4]([O:9][CH3:10])[C:5]([O:7][CH3:8])=[O:6].O[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.N#N>O>[O:22]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[N:12]1[O:1][CH2:2][CH2:3][C@H:4]([O:9][CH3:10])[C:5]([O:7][CH3:8])=[O:6]

Komponenten

7

Edukt 5

HCID 947NitrogenHCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57999131(S)-methyl 4-hydroxy-2-methoxybutanoate

Produkt 1

HCID 67065361(S)-methyl 4-(1,3-dioxoisoindolin-2-yloxy)-2-methoxybutanoateAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl 4-hydroxy-2-methoxybutanoate (46b, 1.48 g, 10.0 mmol) in CH2CT2 (25.0 mL) was added 2-hydroxyisoindolin-1,3-dione (1.63 g, 10.0 mmol) and triphenylphosphine (3.93 g, 15.0 mmol). The resultant mixture was cooled to 0° C. and diisopropylazodicarboxylate (2.95 ml, 15.0 mmol) was slowly added drop wise under N2 atmosphere. The reaction mixture was stirred at ambient temperature for 48 h. To the reaction mixture, H2O (100 mL) was added and extracted with CH2Cl2. The organic layers washed with brine. Dried over anhydrous Na2SO4, filtered and concentrated to provide yellow oil, which was purified by flash chromatography (50% EtOAc-hexane) to afford (S)-methyl 4-(1,3-dioxoisoindolin-2-yloxy)-2-methoxybutanoate (46c, 1.25 g, 42%) as light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.98-2.10 (m, 1H) 2.23-2.37 (m, 1H) 3.51 (s, 3H) 3.79 (s, 3H) 4.24 (dd, J=9.47, 3.66 Hz, 1H) 4.31-4.40 (m, 2H) 7.74-7.82 (m, 2H) 7.81-7.90 (m, 2H).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe organic layers washed with brine
  3. dry with materialDried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide yellow oil, which
  7. customwas purified by flash chromatography (50% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2af7285314ea487fabf7aa697f72b742
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071766B2

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