N-(tert-butoxycarbonyl)glycine → {2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl Ester

HRID 11685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11685
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[F:25][C:26]1[CH:40]=[CH:39][C:29]([CH2:30][N:31]2[CH2:36][C@H:35]([CH3:37])[NH:34][CH2:33][C@H:32]2[CH3:38])=[CH:28][CH:27]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]([N:34]1[CH2:33][C@H:32]([CH3:38])[N:31]([CH2:30][C:29]2[CH:39]=[CH:40][C:26]([F:25])=[CH:27][CH:28]=2)[CH2:36][C@H:35]1[CH3:37])=[O:12])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine

Produkt 1

HCID 69655545{2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl EsterAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butoxycarbonylamino-acetic acid (0.71 g, 4.05 mmol) in dichloromethane (40 mL) was added 4-dimethylaminopyridine (0.74 g, 6.07 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.16 g, 6.07 mmol) and 1-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazine (0.90 g, 4.05 mmol). The reaction was stirred overnight at ambient temperature. The reaction was diluted with dichloromethane and washed with brine. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.45 g).

Aufarbeitung

  1. washwashed with brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7f1d605a00c407485160438a0416ec8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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