Hydrochloric Acid → HCID 19348478、化合物

HRID 1418188ノート

反応式

HRID 1418188 の反応式
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]=[N+]=[N-])=[CH:8][C:7]=1[NH:16][C:17](=[O:35])[CH2:18][CH:19]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:5])([CH3:4])[CH3:3]>CC(C)=O.[Zn]>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:7]=1[NH:16][C:17](=[O:35])[CH2:18][CH:19]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:3])([CH3:4])[CH3:5]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 19348686HCID 19348686、化合物

生成物 1

HCID 19348478HCID 19348478、化合物収率 87.3%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 180Acetone溶媒

実験手順

301 mg (4.60 mmol) of zinc dust and then 5 ml of 2N aqueous hydrochloric acid were added to a solution of 430 mg (0.92 mmol) of N-(2-t-butyl-5-azidomethylphenyl)-3-(2,4-dimethoxyphenyl)octanamide [prepared as described in step (i) above] in 10 ml of acetone, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was filtered to remove zinc dust, and the filtrate was made alkaline by adding a saturated aqueous solution of sodium hydrogencarbonate. The mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 354 mg (yield 86%) of the title compound as a foam-like substance.

後処理

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove zinc dust
  3. additionby adding a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionThe mixture was then extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through 50 g of silica gel using a 10:1
  9. additionby volume mixture of ethyl acetate and methanol as the eluent

出典と根拠

ORDレコード
ord-2bc63b503f704e9ca16de8320d6a54e1
出典データセット
uspto-grants-1999_03
特許番号
US05880147

反応ノート

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