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Diisopropylethylamine → (4R,5R,6R)-5-Acetylamino-4-hydroxy-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

HRID 1603999
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1603999
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:23]([NH:26][C@@H:27]1[C@H:32]([O:33][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:31]=[C:30]([C:51]([O:53]C)=[O:52])[O:29][C@H:28]1[C:55]([O-:57])=O)(=[O:25])[CH3:24].C(N(CC)C(C)C)(C)C.[CH2:67]([CH2:75][CH2:76][CH2:77][NH2:78])[CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>CN(C)C=O>[C:23]([NH:26][C@H:27]1[C@H:28]([C:55](=[O:57])[NH:78][CH2:77][CH2:76][CH2:75][CH2:67][CH2:68][C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[O:29][C:30]([C:51]([OH:53])=[O:52])=[CH:31][C@H:32]1[OH:33])(=[O:25])[CH3:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 140275BenzenepentanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86754843(2R,3S,4R)-3-acetylamino-4-(tert-butyldiphenylsilanyloxy)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid, 6-methyl ester

Produkt 1

HCID 70196688
(4R,5R,6R)-5-Acetylamino-4-hydroxy-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
Ausbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (1.42 g) was added to a solution of (2R,3S,4R)-3-acetylamino-4-(tert-butyldiphenylsilanyloxy)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid, 6-methyl ester (2 g) and N,N-diisopropylethylamine (1.4 ml) in dimethylformamide (5 ml), under nitrogen. To this was added N-phenethylpropylamine (722 mg) and the reaction was stirred at 23° C. for 16 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The organic extracts were dried over anhydrous sodium sulphate and the solvent was removed in vacuo to give a fawn foam. The foam was chromatographed over silica (Merck 9385, 45 g) using medium pressure (ca 4 psi) and ethyl acetate/cyclohexane (1:2 v/v) as the eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a white foam (1.1 g). 1H NMR (250 MHz, CDCl3, rotamers) 7.6--7.1 (15H, m), 6.0+5.95 (1H, 2×m), 5.9--5.8 (1H, 2×d, J=6Hz), 5.2 (1H, 2×d, J=5Hz), 4.6 (1H, 2×d, J=3Hz), 4.0--3.7 (1H, m), 3.8 (3H, 2×s), 3.5--2.9 (4H, m), 2.8+2.5 (2H, 2×m), 2.0 (3H, 2×s), 1.5 --1.2 (2H, m), 1.1 (9H, s), 0.9+0.7 (3H, 2×t, J=7Hz).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. dry with materialThe organic extracts were dried over anhydrous sodium sulphate
  4. customthe solvent was removed in vacuo
  5. customto give a fawn foam
  6. customThe foam was chromatographed over silica (Merck 9385, 45 g)
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d11be401374e46b4a1f14f70b22c542c
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05990156

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