Hydrochloric Acid → Ethyl 9-(2,3-Dichlorophenyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido-[2,3-f][1,4]thiazepine-8-carboxylate

HRID 1461475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461475
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:19]2[S:18](=[O:21])(=[O:20])[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]=2[NH:12][C:11]([CH3:29])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl.[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:19]2[S:18](=[O:20])(=[O:21])[CH2:17][CH2:16][NH:15][CH2:14][C:13]=2[NH:12][C:11]([CH3:29])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15035858HCID 15035858, Verbindung

Produkt 1

HCID 15035859Ethyl 9-(2,3-Dichlorophenyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido-[2,3-f][1,4]thiazepine-8-carboxylateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl 9-(2,3-dichlorophenyl)-4-(t-butyloxycarbonyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido[2,3-f][1,4]thiazepine-8-carboxylate (2.45 g, 4.6 mmole) from Example 7, in ethyl acetate (150 mL) was cooled to 0° C. and saturated with gaseous hydrogen chloride. The mixture was warmed to room temperature. The reaction was then again chilled to 0° C. and shaken with 200 mL of cold 4 N NaOH. The aqueous layer was separated and extracted with 2×100 mL of chloroform. The ethyl acetate layer was dried with brine and the combined organic extracts were dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue triturated with ether to give the product (1.86 g, 94% yield).

Aufarbeitung

  1. temperatureThe reaction was then again chilled to 0° C.
  2. customThe aqueous layer was separated
  3. extractionextracted with 2×100 mL of chloroform
  4. dry with materialThe ethyl acetate layer was dried with brine
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. customThe solvents were evaporated under reduced pressure
  7. customthe residue triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-fb2420e71e6149429b9917273ee2bf1a
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075440

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