Gabapentin → Boc-Asp(OMe) Gabapentin

HRID 28765

반응식

HRID 28765 반응식
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][C:4](=[O:7])[O:5][CH3:6].ON1C(=O)CCC1=O.[CH2:26]1[CH2:31][CH2:30][C:29]([CH2:36][NH2:37])([CH2:32][C:33]([OH:35])=[O:34])[CH2:28][CH2:27]1.C(=O)([O-])O.[Na+]>C(#N)C>[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][C:4](=[O:7])[O:5][CH3:6].[CH2:26]1[CH2:27][CH2:28][C:29]([CH2:36][NH2:37])([CH2:32][C:33]([OH:35])=[O:34])[CH2:30][CH2:31]1

참가 물질

6

반응물 4

HCID 3446GabapentinHCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 10977771(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methoxy-4-oxobutanoic acid

생성물 1

HCID 131727013Boc-Asp(OMe) Gabapentin수율 98%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of Boc-Asp(OMe)-OH (5 g, 20 mmol) in acetonitrile (100 mL) was added N-hydroxysuccinimide (2.53 g, 22 mmol) and N,N-dicyclohexylcarbodiimide (4.5 g, 22 mmol). The reaction was stirred at ambient temperature for 4 h. The reaction mixture was filtered directly into an aqueous solution (100 mL) of gabapentin (3.77 g, 22 mmol) and sodium hydrogencarbonate (1.85 g, 22 mmol) and the resulting mixture stirred at ambient temperature for 16 h. The reaction was concentrated under reduced pressure, the residue dissolved in ethyl acetate/diethyl ether (1:1, 300 mL) and washed with 0.1M aqueous potassium hydrogensulfate (2×500 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure to afford Boc-Asp(OMe)-Gabapentin as a white solid (7.8 g, 19.5 mmol, 98%).

후처리

  1. stirringthe resulting mixture stirred at ambient temperature for 16 h
  2. concentrationThe reaction was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate/diethyl ether (1:1, 300 mL)
  4. washwashed with 0.1M aqueous potassium hydrogensulfate (2×500 mL)
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-a5352857d5b9435d9c482e161179277d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420002B2

연결된 노트

불러오는 중…