Triethylamine → HCID 57629160, Verbindung

HRID 502925

Reaktionsgleichung

Reaktionsgleichung von HRID 502925
[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][NH:5]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]>C(Cl)Cl>[C:18]([C:20]1[CH:21]=[C:22]([S:26]([N:5]2[CH2:6][C@@H:7]([OH:9])[CH2:8][C@H:4]2[C:3]([O:2][CH3:1])=[O:10])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)#[N:19]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 57629160HCID 57629160, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of cis-4-hydroxy-L-proline methyl ester (10.0 g, 68.8 mmol), triethylamine (13.9 g, 138 mmol), and CH2Cl2 (200 mL) was added 3-cyanobenzene-1-sulfonyl chloride (13.9 g, 68.8 mmol). After 1 h, the reaction was partitioned between saturated aqueous NaHCO3 (75 mL) and CH2Cl2 (100 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×75 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified on silica gel (1:99→30:70 ethyl acetate-hexanes) to afford the title compound as a colorless crystalline solid: 1H NMR (500 MHz, CDCl3) δ 8.19-8.18 (m, 1H), 8.13-8.11 (m, 1H), 7.89-7.85 (m, 1H), 7.69-7.65 (t, 1H), 4.52-4.50 (m, 1H), 4.44-4.43 (m, 1H), 3.67 (s, 3H), 3.52 (dd, 1H), 3.47-3.41 (m, 1H), 3.1 (d, 1H), 2.33-2.27 (m, 1H), 2.20-2.17 (m, 1H); LRMS (ESI) m/z 311 (311 calcd for C13H14N2O5S, M+H).

Aufarbeitung

  1. customthe reaction was partitioned between saturated aqueous NaHCO3 (75 mL) and CH2Cl2 (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×75 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (1:99→30:70 ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b196d50604564e0a928f54e259062ada
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776891B2

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