Potassium Carbonate → Tert-butyl 4-((2-(4-(methoxycarbonyl)phenyl)-5-methyloxazol-4-yl)methylthio)piperidine-1-carboxylate

HRID 931473

Reaktionsgleichung

Reaktionsgleichung von HRID 931473
[SH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[CH2:16][C:17]1[N:18]=[C:19]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[O:20][C:21]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:30][O:29][C:27]([C:26]1[CH:25]=[CH:24][C:23]([C:19]2[O:20][C:21]([CH3:22])=[C:17]([CH2:16][S:1][CH:2]3[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)[N:18]=2)=[CH:32][CH:31]=1)=[O:28]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

Produkt 1

HCID 68277984Tert-butyl 4-((2-(4-(methoxycarbonyl)phenyl)-5-methyloxazol-4-yl)methylthio)piperidine-1-carboxylateAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of the crude tert-butyl 4-mercaptopiperidine-1-carboxylate (2.34 g, 10.78 mmol, 1.20 equiv), methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (2.33 g, 8.79 mmol, 1.00 equiv) and potassium carbonate (1.74 g, 12.39 mmol, 1.50 equiv) in N,N-dimethylformamide (23.4 mL) was stirred overnight in a 100-mL round-bottom flask at 50° C. The reaction mixture was then quenched by the addition of 30 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 2×40 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was eluted with ethyl acetate/petroleum ether (1:30-1:5) on a silica gel column to give 920 mg (23%) of tert-butyl 4-((2-(4-(methoxycarbonyl)phenyl)-5-methyloxazol-4-yl)methylthio)piperidine-1-carboxylate as a yellow solid. LC-MS: (ES, m/z): 447 [M+H]+, 347, 271, 146, 105.

Aufarbeitung

  1. customThe reaction mixture was then quenched by the addition of 30 mL of water
  2. extractionThe resulting solution was extracted with 3×30 mL of ethyl acetate
  3. washThe organic layer was washed with 2×40 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. washThe residue was eluted with ethyl acetate/petroleum ether (1:30-1:5) on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-cd9d38ee9b76483ebcf697ff6bd4ef0f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296732B2

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