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 2353911노트

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HRID 2353911 반응식
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]

참가 물질

5

반응물 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

생성물 1

HCID 686772987-Bromo-8-chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester수율 80.3%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 962Water용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-560fa6d66b474124ac5ae55ed3aad339
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749992B2

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