Beta-Alanine → N-carboxyethyl-amphetamine

HRID 2372880

反応式

HRID 2372880 の反応式
[C:1]1([CH2:7][C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[C:14]([CH2:13][CH2:12][NH:11][CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:9])([OH:16])=[O:15]

参加物

6

反応物 3

HCID 239Beta-AlanineHCID 7678PhenylacetoneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 14463243N-carboxyethyl-amphetamine収率 60.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Phenylacetone (100 mg, 0.745 mmol) was dissolved in anhydrous methanol (2.0 ml). Beta-alanine (398 mg, 4.47 mmol) was added, followed by sodium cyanoborohydride (94 mg, 1.49 mmol). After 18 hours of stirring under nitrogen, the reaction mixture was filtered, and the filtrate solvent was removed in vacuo. The resulting crude material was purified on four 1.0 millimeter C18 reverse-phase preparative thin layer chromatography plates eluted with H2O/methanol/acetic acid (40/60/0.4). The material obtained was dissolved in ethyl acetate (20 ml) and was extracted with 1.0M sodium bicarbonate (3×20 ml). The aqueous extracts were combined, the pH was adjusted to 4 with 1.0M hydrochloric acid, and the solvent was removed in vacuo. The resulting crystalline solid was then triturated twice with 50-milliliter portions of ethyl acetate and filtered. The filtrates were combined, and the solvent was removed in vacuo to yield 93 milligrams of N-carboxyethyl-amphetamine.

後処理

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate solvent was removed in vacuo
  3. customThe resulting crude material was purified on four 1.0 millimeter C18 reverse-phase preparative thin layer chromatography plates
  4. washeluted with H2O/methanol/acetic acid (40/60/0.4)
  5. customThe material obtained
  6. extractionwas extracted with 1.0M sodium bicarbonate (3×20 ml)
  7. customthe solvent was removed in vacuo
  8. customThe resulting crystalline solid was then triturated twice with 50-milliliter portions of ethyl acetate
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-672d7e4cf34d4e9999d8f5472e7f45ad
出典データセット
uspto-grants-1992_03
特許番号
US05101015

関連ノート

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