Hydrochloric Acid → HCID 46862166、化合物

HRID 411264

反応式

HRID 411264 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([NH:19]C(=O)C)(C(OCC)=O)[C:9]([O:11][CH2:12]C)=[O:10])[CH:2]=1.[ClH:23]>>[ClH:23].[ClH:23].[CH3:12][O:11][C:9](=[O:10])[C@H:8]([CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[NH2:19]

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 13817914Diethyl acetamido[(pyridin-3-yl)methyl]propanedioate

生成物 1

HCID 46862166HCID 46862166、化合物収率 100%

実験手順

Sodium metal (1.40 g, 61 mmol) was dissolved in EtOH (100 mL) containing diethyl acetamidomalonate (6.62 g, 30.5 mmol) and 3-picolyl chloride hydrochloride (5.00 g, 30.5 mmol) were added. The mixture was heated to reflux for 6 hr, and then cooled and filtered to remove NaCl (washed with EtOH). The solvent was removed in vacuo and the mixture was taken up into saturated aqueous NaHCO3 (100 mL) and extracted with EtOAc (3×100 mL). The solvent was removed and the residue purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH) to give diethyl 2-(3-pyridylmethyl)-2-acetamidomalonate (2.84 g, 30%). Diethyl 2-(3-pyridylmethyl)-2-acetamidomalonate was dissolved in 6N HCl (30 mL) and heated to reflux for 19 hr whereupon it was cooled to room temperature and the HCl solution was removed by evaporation in vacuo. The intermediate amino acid dihydrochloride salt was taken up into MeOH (30 mL) saturated with HCl gas and stirred for 3.5 hr. The MeOH/HCl was removed by evaporation in vacuo to give β-(3-pyridyl)alanine methyl ester dihydrochloride (2.235 g, 100%).

後処理

  1. temperatureheated
  2. temperatureto reflux for 19 hr whereupon it
  3. customthe HCl solution was removed by evaporation in vacuo
  4. customThe MeOH/HCl was removed by evaporation in vacuo

出典と根拠

ORDレコード
ord-1b5c8ad3d7c24bf385cd10a2f9f3eee8
出典データセット
uspto-grants-2003_05
特許番号
US06559127B1

関連ノート

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