m-Chloroperbenzoic acid → tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno(2,3-b]pyridin-4-yl}phenoxy)-acetate

HRID 1830844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830844
[Cl:1][C:2]1[C:3]([C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:25][CH:24]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21][CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].ClC1C=CC=C(C(OO)=[O:46])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[CH:25][CH:24]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21](=[O:46])[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:10](=[O:15])[CH2:11][CH2:12][C:13]1=[O:14]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 86588675tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-5,8-dihydro-6H-thiopyrano[4',3':4,5]-thieno[2,3-b]pyridin-4-yl}phenoxy)acetate

Produkt 1

HCID 86588674tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno(2,3-b]pyridin-4-yl}phenoxy)-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Example 112 (2.7 g) in methylene chloride (50 ml) was added m-chloroperbenzoic acid (70%, 1.2 g) under ice-cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and then water and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4′,3′:4,5]thieno[2,3-b]pyridin-4-yl}phenoxy)-acetate from the fraction eluted with ethyl acetate. It was recrystallized from ethyl acetate-hexane (2.2 g, 79%). Colorless prisms. Melting point 175–176° C.

Aufarbeitung

  1. temperaturecooling
  2. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution
  3. dry with materialwater and dried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7e28b9e80c3f479b8a8c004c3f57495c
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067527B2

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