Acetic Anhydride → Benzyl 3-acetamido-4-oxopentanoate

HRID 1585648

反応式

HRID 1585648 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=O)=[O:10])=[CH:3][CH:2]=1.[CH2:17](N(CC)CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25].[OH-].[K+]>CN(C)C1C=CN=CC=1.O>[C:24]([NH:16][CH:12]([C:13](=[O:15])[CH3:17])[CH2:11][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:10])(=[O:26])[CH3:25]

参加物

7

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 1011864-(Phenylmethyl) hydrogen L-aspartate

生成物 1

HCID 22220883Benzyl 3-acetamido-4-oxopentanoate収率 82.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒

実験手順

β-Benzyl L-aspartate (400 g, 1.79 mol) was suspended in triethylamine (748 ml, 5.37 mol) and acetic anhydride (676 ml, 7.16 mol) was dropwise added at 0° C. with stirring. After stirring for 30 minutes, 4-dimethylaminopyridine (20.0 g, 0.16 mol) was portionwise added under ice-cooling. The mixture was stirred overnight at room temperature, and ice was added under ice-cooling. At the end of the exothermic process, water (700 ml) was added. A 7.5N aqueous solution of potassium hydroxide was portionwise added to make its pH 9. The mixture was extracted three times with ethyl acetate (1,000 ml), and the organic layer was washed twice with 1N hydrochloric acid (1,000 ml), twice with a saturated aqueous solution of sodium hydrogencarbonate (500 ml) and with saturated brine (500 ml) in order. The layer was dried over magnesium sulfate and concentrated to dryness to give 390 g of the title compound.

後処理

  1. stirringAfter stirring for 30 minutes
  2. temperaturecooling
  3. stirringThe mixture was stirred overnight at room temperature
  4. additionice was added under ice-
  5. temperaturecooling
  6. extractionThe mixture was extracted three times with ethyl acetate (1,000 ml)
  7. washthe organic layer was washed twice with 1N hydrochloric acid (1,000 ml), twice with a saturated aqueous solution of sodium hydrogencarbonate (500 ml) and with saturated brine (500 ml) in order
  8. dry with materialThe layer was dried over magnesium sulfate
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-7b368e359401416fae1a774b23781dcc
出典データセット
uspto-grants-1999_08
特許番号
US05939445

関連ノート

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