Pyridine → HCID 58472432, Verbindung

HRID 547574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547574
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][C@H:11]([OH:12])[CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].N1C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[S:33]([O:12][CH:11]1[CH2:13][N:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:2]([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH2:10]1)([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 58472432HCID 58472432, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of Boc-Hyp-OtBu (0.5 g, 1.74 mmol) in DCM (20 mL) were added pyridine (0.550 g, 6.96 mmol) and p-toluenesulfonyl chloride (0.663 g, 3.48 mmol) at r.t. After being stirred at r.t. for 24 h, the reaction mixture was quenched with 1M HCl and extracted with DCM. The organic layer was successively washed with 1M HCl, water, brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica gel and provided pure product, Cpd C (yellow solid). Spectral Data: 1H-NMR (CDCl3/400 MHz): 7.82 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 5.05 (m, 1H), 4.28 (m, 1H), 3.59 (m, 2H), 2.49 (s, 3H), 2.57 (m, 1H), 2.13 (m, 1H), 1.47 (s, 9H), 1.45 (s, 9H). MS (ES+, m/z): 442.2 (M++1, 30.0).

Aufarbeitung

  1. customthe reaction mixture was quenched with 1M HCl
  2. extractionextracted with DCM
  3. washThe organic layer was successively washed with 1M HCl, water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica gel
  7. customprovided pure product, Cpd C (yellow solid)

Quellen und Nachweise

ORD-Eintrag
ord-8c572b163f8642a68e02c0ae638f8466
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939546B2

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