Acetic Acid → HCID 131730872, Verbindung

HRID 43853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43853
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C([BH3-])#N.[Na+].[Cl:17][C:18]1[N:19]=[C:20]([C:25]([NH:27][CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][C:29]2=O)=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24]>O1CCCC1.CO>[C:37]([O:36][C:34]([N:31]1[CH2:30][CH2:29][C@@H:28]([NH:27][C:25]([C:20]2[NH:21][C:22]([CH2:23][CH3:24])=[C:18]([Cl:17])[N:19]=2)=[O:26])[C@H:33]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:32]1)=[O:35])([CH3:40])([CH3:39])[CH3:38].[CH2:1]([NH:8][C@H:29]1[C@@H:28]([NH:27][C:25]([C:20]2[NH:21][C:22]([CH2:23][CH3:24])=[C:18]([Cl:17])[N:19]=2)=[O:26])[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:30]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 68406285tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate

Produkt 1

HCID 131730872HCID 131730872, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzylamine (70 μL, 0.64 mmol), acetic acid (68.7 μL, 1.20 mmol) and sodium cyanoborohydride (42 mg, 0.667 mmol) were added to a mixed solution of tert-butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate obtained in Example (201c) (99 mg, 0.267 mmol) in tetrahydrofuran (3 mL) and methanol (3 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the residue, followed by extraction with ethyl acetate. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate, and then the insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 v/v) to obtain 26 mg of the cis isomer of the title compound (21%) as a colorless solid and 50 mg of the trans isomer of the title compound (41%) as a colorless solid. cis-form

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe insoluble matter was separated by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-2cfd4b8998174a058d33b49656031d61
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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