Hydrochloric Acid → (3S)-1-Acetyl-N-{(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}piperidine-3-carboxamide

HRID 656346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656346
[Cl:1][C:2]1[C:3]([CH3:33])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26](OC(C)(C)C)=[O:27])[CH2:21]3)=[O:19])[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.[C:35](O)(C(F)(F)F)=O>O1CCOCC1.CO>[C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:20]([C:18]([NH:17][C@H:13]2[CH2:14][CH2:15][CH2:16][N:11]([S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[CH3:33])(=[O:9])=[O:10])[CH2:12]2)=[O:19])[CH2:21]1)(=[O:27])[CH3:35]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58656262tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate

Produkt 1

HCID 11554020(3S)-1-Acetyl-N-{(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}piperidine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]-piperidine-1-carboxylate (10.0 mg, 200 μmol) was treated with 4.0 M of hydrogen chloride in 1,4-dioxane (0.5 mL) at rt for 1 h. The volatiles were removed in-vacuo and the residue was dissolved in acetonitrile (0.8 mL) and was treated with diisopropylethylamine (20.0 μL) and acetyl chloride (5.0 μL). The crude reaction mixture was diluted with MeOH (1.3 mL) and was adjusted to a pH of 2 using TFA and was purified by prep-HPLC to give the desired product. LCMS: (M+H)+=442.1/444.1.

Aufarbeitung

  1. customThe volatiles were removed in-vacuo
  2. dissolutionthe residue was dissolved in acetonitrile (0.8 mL)
  3. additionwas treated with diisopropylethylamine (20.0 μL) and acetyl chloride (5.0 μL)
  4. customThe crude reaction mixture
  5. customwas purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-af285fc49d3a4407be18171ff947ad82
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071624B2

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