4-Methylmorpholine → N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide

HRID 1018462

Reaktionsgleichung

Reaktionsgleichung von HRID 1018462
[CH2:1]([O:8][C:9](=[O:23])[C@H:10]([CH2:19][C:20]([OH:22])=[O:21])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CN1CCOCC1.C[N:38]([C:40]([O:44]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[CH2:1]([O:8][C:9](=[O:23])[C@H:10]([CH2:19][C:20]([OH:22])=[O:21])[NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([C:40]([NH2:38])=[O:44])[CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7017887(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acid

Produkt 1

HCID 70086528N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester (1 g) and piperidine (0.32 mL) in acetonitrile (15 mL) was allowed to react with N-methylmorpholine (0.42 mL) and TBTU (1.2 g) for 6 hr at room temperature. The solvent was removed and the residue, dissolved in EtOAc, was sequentially washed with 2% aqueous hydrochloric acid, saturated aq. NaHCO3 and brine. After drying (Na2SO4) and rotoevaporation, the resulting yellowish oil was purified by flash chromatography over silica to obtain N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester-4-piperidinamide (900 mg) as a colorless oil.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionthe residue, dissolved in EtOAc
  3. washwas sequentially washed with 2% aqueous hydrochloric acid, saturated aq. NaHCO3 and brine
  4. dry with materialAfter drying (Na2SO4) and rotoevaporation
  5. customthe resulting yellowish oil was purified by flash chromatography over silica

Quellen und Nachweise

ORD-Eintrag
ord-60c005376dde4530a849137725f3e1dc
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06482827B1

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