Methanesulfonyl chloride → HCID 10861453, Verbindung

HRID 399514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399514
[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@@H:10]([O:12][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 10861453HCID 10861453, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline tert-butyl ester (573 mg, 1.99 mmol) in pyridine (3.5 mL) cooled to 0° C. was added methanesulfonyl chloride (0.31 mL, 3.99 mmol). The reaction mixture was stirred for 2 hours at ice temperature, diluted with ethyl acetate (30 mL), washed with 1M sodium hydrogencarbonate solution, 1M citric acid, water, dried (Na2SO4), and evaporated. The crude product was purified by flash silica gel chromatography eluting with 1% methanol/dichloromethane; yield 686 mg (94%). 400 MHz 1H NMR (CDCl3): δ1.42-1.44 (2s, 18H); 2.20 (m, 1H); 2.60 (m, 1H); 3.02 (s, 3H); 3.68-3.86 (m, 2H); 4.29 (m, 1H); 5.22 (m, 1H).

Aufarbeitung

  1. washwashed with 1M sodium hydrogencarbonate solution, 1M citric acid, water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe crude product was purified by flash silica gel chromatography
  5. washeluting with 1% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3e7049f39c0d4db8bbce345cdc0ee0e8
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821261

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