N-(2-aminoethyl)acetamide → N-Acetyl-N'-[2-(phenylmethoxy)-2-oxoethyl]ethylenediamine

HRID 482936ノート

反応式

HRID 482936 の反応式
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH:2]=O.[C:13]([NH:16][CH2:17][CH2:18][NH2:19])(=[O:15])[CH3:14]>O1CCCC1>[C:13]([NH:16][CH2:17][CH2:18][NH:19][CH2:2][C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4])(=[O:15])[CH3:14]

参加物

4

反応物 2

HCID 66082N-(2-aminoethyl)acetamideHCID 11008258Benzyl glyoxylate

生成物 1

HCID 20243518N-Acetyl-N'-[2-(phenylmethoxy)-2-oxoethyl]ethylenediamine収率 38.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Benzyl glyoxylate (3.28 g, 20.0 mmol) in dry tetrahydrofuran (15 ml) was added dropwise in monoacetylethylenediamine (1.53 g, 15 mmol) in dry tetrahydrofuran (60 ml) at room temperature. After 2 hours, the tetrahydrofuran was removed under vacuum, and the residue was dissolved in dry methanol (100 ml). Upon cooling to 0° C., 1.55 g of sodium cyanoborohydride was added, immediately followed by dropwise addition of 1.54 ml of acetic acid. The reaction was allowed to warm to room temperature and stirred for 40 minutes. The volatiles were removed under vacuum, and the residue was extracted from aqueous sodium bicarbonate with ethyl acetate. The combined organic layers were dried with sodium sulfate, and the volatiles were removed. The residue was purified by column chromatography on silica (LPS-1) (loading with 2% methanol/dichloromethane and eluting with 5% methanol/dichloromethane to yield 1.46 g of the title compound.

後処理

  1. customthe tetrahydrofuran was removed under vacuum
  2. dissolutionthe residue was dissolved in dry methanol (100 ml)
  3. addition1.55 g of sodium cyanoborohydride was added
  4. additionimmediately followed by dropwise addition of 1.54 ml of acetic acid
  5. temperatureto warm to room temperature
  6. customThe volatiles were removed under vacuum
  7. extractionthe residue was extracted from aqueous sodium bicarbonate with ethyl acetate
  8. dry with materialThe combined organic layers were dried with sodium sulfate
  9. customthe volatiles were removed
  10. customThe residue was purified by column chromatography on silica (LPS-1) (loading with 2% methanol/dichloromethane
  11. washeluting with 5% methanol/dichloromethane

出典と根拠

ORDレコード
ord-a5e5a39da5a64d26bff0345ab6c1df01
出典データセット
uspto-grants-1986_03
特許番号
US04576749

反応ノート

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