Thiophenol → (2S)-tert-butyl 5-((allyloxy)amino)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627198
[CH2:1]([O:4][N:5]([CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31](=[O:33])[NH2:32])[CH:20]=[C:19]1[CH2:34][C:35]([NH2:37])=[O:36])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31](=[O:33])[NH2:32])[CH:20]=[C:19]1[CH2:34][C:35]([NH2:37])=[O:36])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89852287(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate2×

Produkt 1

HCID 89851408(2S)-tert-butyl 5-((allyloxy)amino)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 175, 1.36 g, 2.52 mmol) and potassium carbonate (1.742 g, 12.60 mmol) in acetonitrile (20.0 mL) at 0° C. was added benzenethiol (1.389 g, 12.60 mmol). The mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated and the resulting residue was triturated with DCM. The solids were removed by filtration. The filtrate was concentrated to a pale yellow film, which was subjected to silica gel column eluting with 0-50% MeOH/DCM to give a pale yellow solid, 330 mg, 36.9%.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was triturated with DCM
  3. customThe solids were removed by filtration
  4. concentrationThe filtrate was concentrated to a pale yellow film, which
  5. washeluting with 0-50% MeOH/DCM
  6. customto give a pale yellow solid, 330 mg, 36.9%

Quellen und Nachweise

ORD-Eintrag
ord-c2df155884504cec9e5f3000576e0f63
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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