Beta-Alanine → N-carboxyethyl-amphetamine

HRID 6438

반응식

HRID 6438 반응식
[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]

참가 물질

6

반응물 3

HCID 239Beta-AlanineHCID 7678PhenylacetoneHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 14463243N-carboxyethyl-amphetamine수율 60.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-478badbfe80b4ba79d32c3a102b14cc6
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248791

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