N-Methylbenzylamine → 3-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-4(S)-isopropyl-2-oxazolidinone

HRID 1768858노트

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HRID 1768858 반응식
[CH2:1]([C@H:8]([CH2:20][C:21]([O:23]CC1C=CC=CC=1)=O)[C:9]([N:11]1[C@@H:15]([CH:16]([CH3:18])[CH3:17])[CH2:14][O:13][C:12]1=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([NH:38][CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>C(O)C.[Pd]>[CH2:1]([C@H:8]([CH2:20][C:21]([N:38]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:39])=[O:23])[C:9]([N:11]1[C@@H:15]([CH:16]([CH3:18])[CH3:17])[CH2:14][O:13][C:12]1=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 144294593-[2(R)-Benzyl-3-(benzyloxycarbonyl)propionyl]-4(S)-isopropyl-2-oxazolidinone

생성물 1

HCID 150457533-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-4(S)-isopropyl-2-oxazolidinone수율 98%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 1.03 g (2.52 mmole) of 3-[2(R)-benzyl-3-(benzyloxycarbonyl)propionyl]-4(S)-isopropyl-2-oxazolidinone (prepared as described in Preparation 13) in 20 ml of ethanol was stirred at room temperature for 4 hours under an atmosphere of hydrogen and in the presence of 100 mg of 10% w/w palladium-on-charcoal. The catalyst was then removed by filtration, and the filtrate was concentrated by distillation under reduced pressure. The residue was dissolved in 50 ml of anhydrous tetrahydrofuran, and 0.39 ml (3.02 mmole) of N-benzyl-N-methylamine, 0.46 ml of 95% diethyl cyanophosphonate and 0.42 ml of triethylamine were added, in that order, to the solution, whilst ice-cooling and under an atmosphere of nitrogen, after which the mixture was stirred for 6 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure column chromatography through silica gel using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent), followed by recrystallization from diisopropyl ether, to afford 1.04 g (yield 98%) of the title compound as white crystals, melting at 60°-62° C.

후처리

  1. customThe catalyst was then removed by filtration
  2. concentrationthe filtrate was concentrated by distillation under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of anhydrous tetrahydrofuran
  4. temperaturecooling and under an atmosphere of nitrogen
  5. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  6. customthe residue was purified by medium pressure column chromatography through silica gel using a 1:1
  7. additionby volume mixture of ethyl acetate and hexane as the eluent),
  8. customfollowed by recrystallization from diisopropyl ether

출처 및 근거

ORD 기록
ord-bbcb2995c9f34d4cad349e1471ef5e43
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378689

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