Piperidine-2-carboxylic acid tert-butylamide → 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide

HRID 466853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466853
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:26]1[O:28][CH2:27]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@H:26]([OH:28])[CH2:27][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]1[C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 5289197Piperidine-2-carboxylic acid tert-butylamideHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Produkt 1

HCID 569781971-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamideAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2.576 g of N-tert.butyl-2(S)-piperidinecarboxamide and 4.158 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane in 70 ml of ethanol was heated at reflux for 16 hours. The solvent was removed by evaporation and the residue was dissolved in 100 ml of diethyl ether and treated with 10 g of activated magnesium silicate. The solvent was then removed by evaporation and there were obtained 6.16 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide as a colourless glass; MS: m/e 482 [M+H]+.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in 100 ml of diethyl ether
  4. additiontreated with 10 g of activated magnesium silicate
  5. customThe solvent was then removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-72a5c081ee9b41639189f979b2248143
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157041

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