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Dimethylamine → N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-threoninamide

HRID 1620711
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HRID 1620711 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C@@H:10]([CH3:13])[O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][CH3:19].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:18]([CH3:19])[CH3:17])=[O:16])[C@@H:10]([CH3:13])[O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

7

반응물 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15460346(2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acid

생성물 1

HCID 86678875N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-threoninamide수율 77.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(tert-butoxycarbonyl)-O-methyl-L-threonine (2.33 g), 50% aqueous dimethylamine solution (1.08 g) and N-ethyl-N-(1-methylethyl)propan-2-amine (2.58 g) in DMF (30 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (4.18 g) under ice-cooling. The reaction mixture was stirred at room temperature overnight, the reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.02 g).

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-8478cf14c7dd43728cab134aab6c8c2c
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772277B2

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