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 2353911ノート

反応式

HRID 2353911 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-560fa6d66b474124ac5ae55ed3aad339
出典データセット
uspto-grants-2010_07
特許番号
US07749992B2

反応ノート

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