Water → tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate

HRID 43846

Reaktionsgleichung

Reaktionsgleichung von HRID 43846
C(N(CC)CC)C.[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@@H:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][C@H:20]2[OH:32])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15].O>CS(C)=O.ClCCl>[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][C:20]2=[O:32])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]

Komponenten

6

Edukt 3

HCID 962WaterHCID 8471TriethylamineHCID 86648545tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 68406285tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylateAusbeute 120,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (374 μL, 2.68 mmol) and sulfur trioxide-pyridine complex (256 mg, 1.61 mmol) were added to a mixed solution of tert-butyl trans(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate synthesized in Example (201b) (100 mg, 0.268 mmol) in dimethyl sulfoxide (1 mL) and dichloromethane (1 mL) at room temperature, and the mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain 120 mg of the title compound as an orange foamy substance, which was used for the next reaction without purification.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-776f04e516aa4eaeaf533d0bcbc52b92
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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