4-Methylmorpholine → Methyl (3S)-4-{[4-(2,3-butadienyloxy)phenyl]sulfonyl}-2,2-dimethyl-3-thiomorpholinecarboxylate

HRID 1180550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180550
[CH3:1][C:2]1([CH3:12])[S:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]([O:10][CH3:11])=[O:9].CN1CCOCC1.[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH:21]=[C:22]=[CH2:23]>C(Cl)Cl>[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([N:4]2[CH2:5][CH2:6][S:7][C:2]([CH3:12])([CH3:1])[C@@H:3]2[C:8]([O:10][CH3:11])=[O:9])(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH:21]=[C:22]=[CH2:23]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 18345630methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylateHCID 552804204-(2,3-Butadienyloxy)benzenesulfonyl chloride

Produkt 1

HCID 86588660Methyl (3S)-4-{[4-(2,3-butadienyloxy)phenyl]sulfonyl}-2,2-dimethyl-3-thiomorpholinecarboxylateAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of product from Example 23 (155 mg, 0.82 mmol) in methylene chloride (5 ml) was added N-methylmorpholine (0.180 ml, 1.64 mmol) followed by the product from Example 5 (200 mg, 0.82 mmol). The resulting mixture was stirred for 15 hours at room temperature. The solvent was removed in vacuo and the residue dissolved in ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride and dried over anhydrous sodium sulfate. The crude residue was purified by flash chromatography to give 170 mg (52%) of the product.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-44be6d97419545ad978f46b37b8b0f45
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282496B2

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