Trifluoroacetic acid → (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627168
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([CH2:31][O:32][CH3:33])[CH:20]=[C:19]1[C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:4][N:5]([C@@H:18]1[C:19]([C:34]([N:35]([CH3:37])[CH3:36])=[O:38])=[CH:20][C@@H:21]([CH2:31][O:32][CH3:33])[NH:22][CH2:23]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 89851960(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1 (2H)-carboxylate2×

Produkt 1

HCID 89851925(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamideAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 140, 1.642 g, 2.96 mmol) in DCM (8 mL) was added trifluoroacetic acid (4.33 mL, 56.25 mmol) and stirred at rt for 30 minutes. Upon addition, the color of the solution immediately turned pink. Then the solvents were evaporated and the crude product redissolved in DCM and washed with 0.5N NaOH, brine, filtered and concentrated to obtain the desired product (1.346 g, 100%) as a beige foam.

Aufarbeitung

  1. additionUpon addition
  2. customThen the solvents were evaporated
  3. dissolutionthe crude product redissolved in DCM
  4. washwashed with 0.5N NaOH, brine
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e066778b96a2463ca84a14b48d3deb51
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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