7-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1,4-dicarboxylic acid 1-isopropyl ester 4-methyl ester → 7-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester

HRID 2353911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353911
COC([CH:5]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])[C:8]2[CH:18]=[C:19]([Cl:23])[C:20]([Br:22])=[CH:21][C:7]=2[C:6]1=[O:24])=O>CC(O)=O.Cl.O>[CH:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH2:5][C:6](=[O:24])[C:7]2[CH:21]=[C:20]([Br:22])[C:19]([Cl:23])=[CH:18][C:8]1=2)=[O:13])([CH3:17])[CH3:16]

Komponenten

5

Edukt 1

HCID 686781067-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1,4-dicarboxylic acid 1-isopropyl ester 4-methyl ester

Produkt 1

HCID 686772987-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl esterAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 7-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1,4-dicarboxylic acid 1-isopropyl ester 4-methyl ester (1.43 g, 3.42 mmol) in HOAc (30.0 ml), concentrated HCl (9.00 ml) and water (3.00 ml) was heated at 100° C. for 4 hours and then cooled down to room temperature overnight. The solvents were evaporated under reduced pressure, and the residue was partitioned between ethyl acetate (100 ml) and saturated NaHCO3 (aq) (100 ml). The aqueous layer was extracted with more ethyl acetate (20.0 ml). The combined organics washed with brine (3×120 ml), dried over Na2SO4, filtered and concentrated. The material obtained was subjected to the conditions described in step 2 to provide 7-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (0.990 g, 80%) as white solid. MS (ES+): 360, 362 (M+H).

Aufarbeitung

  1. temperaturecooled down to room temperature overnight
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (100 ml) and saturated NaHCO3 (aq) (100 ml)
  4. extractionThe aqueous layer was extracted with more ethyl acetate (20.0 ml)
  5. washThe combined organics washed with brine (3×120 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material obtained

Quellen und Nachweise

ORD-Eintrag
ord-560fa6d66b474124ac5ae55ed3aad339
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749992B2

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