Water → HCID 57629160, Verbindung

HRID 2108327

Reaktionsgleichung

Reaktionsgleichung von HRID 2108327
[OH:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.C(N(CC)CC)C.[C:18]([C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)#[N:19].O>C(Cl)Cl.C(OCC)(=O)C>[C:18]([C:20]1[CH:21]=[C:22]([S:26]([N:5]2[CH2:6][C@@H:2]([OH:1])[CH2:3][C@H:4]2[C:7]([O:9][CH3:10])=[O:8])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)#[N:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 7021050methyl (2S,4S)-4-hydroxypyrrolidine-2-carboxylate

Produkt 1

HCID 57629160HCID 57629160, VerbindungAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl (4S)-4-hydroxyprolinate (52.0 g, 0.286 mol) was dissolved in 500 mL CH2Cl2 and cooled to 0° C. Triethylamine (83.6 mL, 0.600 mol) was added, followed by 3-cyanobenzenesulfonyl chloride (55.0, 0.273 mol) slowly. The reaction mixture was stirred at room temperature overnight. Water was added, and the aqueous layer was extracted three times with CH2Cl2. The combined organic layers were washed with 1N HCl, H2O, 1N NaOH, and brine, dried over MgSO4, and concentrated to give a viscous residue. Ethyl acetate (300 mL) was added to completely dissolve the residue. Approximately 100 mL hexanes was added slowly until the solution became slightly cloudy. The mixture was then stirred overnight to allow the product to precipitate. The solid was filtered and rinsed two times with 30% EtOAc/hexanes to give the desired product as an off-white powder (66.2 g, 78%). 1H-NMR (CDCl3, 500 MHz) δ 8.20-8.18 (m, 1H), 8.15-8.12 (m, 1H), 7.92-7.89 (m, 1H), 7.72 (t, 1H), 4.51-4.47 (m, 1H), 4.42 (br s, 1H), 3.74 (s, 3H), 3.53-3.49 (m, 1H), 3.46-3.43 (m, 1H), 3.39 (br s, 1H), 2.29-2.25 (m, 1H), 2.21-2.02 (m, 1H). MS (ESI) calculated for C13H14N2O5S 310.3, observed m/e 311.2 (MH+).

Aufarbeitung

  1. extractionthe aqueous layer was extracted three times with CH2Cl2
  2. washThe combined organic layers were washed with 1N HCl, H2O, 1N NaOH, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a viscous residue
  6. dissolutionto completely dissolve the residue
  7. stirringThe mixture was then stirred overnight
  8. customto precipitate
  9. filtrationThe solid was filtered
  10. washrinsed two times with 30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5cd4557567e846499fe20129834bdafb
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514409B2

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