Thioacetic acid → HCID 90199365, Verbindung

HRID 524905

Reaktionsgleichung

Reaktionsgleichung von HRID 524905
C(OC(/N=N/C(=O)OC(C)C)=O)(C)C.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([F:29])[C:21]=1[N:22]1[CH2:27][CH2:26][CH:25](O)[CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49](=[O:52])([SH:51])[CH3:50]>C1COCC1.C(OC(=O)C)C>[C:49](=[O:52])([S:51][CH:25]1[CH2:26][CH2:27][N:22]([C:21]2[C:20]([F:29])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:15])[CH2:23][CH2:24]1)[CH3:50]

Komponenten

7

Edukt 4

HCID 10484Thioacetic acidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86720960HCID 86720960, Verbindung

Produkt 1

HCID 90199365HCID 90199365, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

isopropyl (NE)-N-isopropoxycarbonyliminocarbamate (723.1 mg, 3.576 mmol) was added dropwise to a solution of 1-(3-chloro-5-fluoro-4-pyridyl)piperidin-4-ol (750 mg, 3.251 mmol) and Triphenylphosphine (937.9 mg, 828.5 μL, 3.576 mmol) in THF at −20° C. After stirring for 15 mins, ethanethioic S-acid (272.2 mg, 255.6 μL, 3.576 mmol) was added, the mixture was allowed to warm to room temperature and was stirred for a further 30 minutes. The mixture was then diluted with ethylacetate (30 ml), washed twice with water (20 ml) and with brine. The organic layer was dried with MgSO4 and concentrated in vacuo to a yellow solid that was purified by column chromatography eluting with 5/95 ether/pet ether to elute side products and then 10/90 ether/pet ether. The relevant fractions were combined and concentrated in vacuo to afford S-(1-(3-chloro-5-fluoropyridin-4-yl)piperidin-4-yl) ethanethioate as a green solid. MS (ES+) 289.0.

Aufarbeitung

  1. stirringwas stirred for a further 30 minutes
  2. washwashed twice with water (20 ml) and with brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. concentrationconcentrated in vacuo to a yellow solid
  5. customthat was purified by column chromatography
  6. washeluting with 5/95 ether/pet ether
  7. washto elute side products
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-084a3e97478741ebbc630aeacb88ad29
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340546B2

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