Dichloromethane → (R)-3-(1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-3-(thiophen-2-yl)propanoic acid

HRID 1625464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625464
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([OH:14])=O)[C:7]1=[O:15].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(Cl)Cl.C(N(CC)C(C)C)(C)C.[NH2:56][C@@H:57]([C:62]1[S:63][CH:64]=[CH:65][CH:66]=1)[CH2:58][C:59]([OH:61])=[O:60]>>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([NH:56][C@@H:57]([C:62]2[S:63][CH:64]=[CH:65][CH:66]=2)[CH2:58][C:59]([OH:61])=[O:60])=[O:14])[C:7]1=[O:15]

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 86717(R)-3-Amino-3-(thiophen-2-yl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534279691-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Produkt 1

HCID 68607579(R)-3-(1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-3-(thiophen-2-yl)propanoic acid

Versuchsvorschrift

Into a round bottom was added 1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (0.400 g, 0.00151 mol;), N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (0.573 g, 0.00151 mol;), Methylene chloride (14 mL, 0.23 mol;), and N,N-Diisopropylethylamine (1310 uL, 0.00754 mol;). The reaction was stirred until all contents were dissolved and preactivation was complete. (R)-3-Amino-3-thiophen-2-yl-propionic acid (0.28 g, 0.0016 mol;) was added and the reaction was allowed to stir for 1-2 hours then an LC-MS was taken which showed product at 1.47. The reaction was worked up by washing with citric acid and brine then drying with magnesium sulfate. The crude concentrated reaction was taken on directly to the next step. ES (+) MS m/e=419.08

Aufarbeitung

  1. dissolutionwere dissolved
  2. stirringto stir for 1-2 hours
  3. washby washing with citric acid and brine
  4. dry with materialthen drying with magnesium sulfate
  5. concentrationThe crude concentrated
  6. customreaction

Quellen und Nachweise

ORD-Eintrag
ord-d701d957f0e941c1b593444ef2e2c688
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778977B2

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