Tetrahydrofuran → N-(2-{3-({(3R)-1-(2-methylbutyl)-3-piperidyl}methyl)amino-3-oxopropyl}amino-2-oxoethyl)-3,3,3-triphenylpropanamide

HRID 394010

Reaktionsgleichung

Reaktionsgleichung von HRID 394010
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][NH:9][C:10](=[O:40])[CH2:11][CH2:12][NH:13][C:14](=[O:39])[CH2:15][NH:16][C:17](=[O:38])[CH2:18][C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:3]1.C(O[BH-](O[C:51](=O)[CH3:52])OC(=O)C)(=O)C.[Na+].O1C[CH2:58][CH2:57][CH2:56]1>CC(CC)C=O.C(OCC)(=O)C>[CH3:56][CH:57]([CH2:51][CH3:52])[CH2:58][N:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][NH:9][C:10](=[O:40])[CH2:11][CH2:12][NH:13][C:14](=[O:39])[CH2:15][NH:16][C:17](=[O:38])[CH2:18][C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:3]1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 69100303N-(2-{3-((3S)-3-piperidylmethyl)amino-3-oxopropyl}amino-2-oxoethyl)-3,3,3-triphenylpropanamide monohydrochloride

Produkt 1

HCID 69100040N-(2-{3-({(3R)-1-(2-methylbutyl)-3-piperidyl}methyl)amino-3-oxopropyl}amino-2-oxoethyl)-3,3,3-triphenylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 72842-MethylbutanalLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 200 mg of N-(2-{3-((3S)-3-piperidylmethyl)amino-3-oxopropyl}amino-2-oxoethyl)-3,3,3-triphenylpropanamide monohydrochloride in 10 ml of tetrahydrofuran, 0.10 ml of 2-methylbutanal and 230 mg of sodium triacetoxyborohydride were successively added at room temperature, followed by 2 hours' stirring at the same temperature. The reaction liquid was diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate solution and saturated saline solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by means of silica gel column chromatography (eluting solvent: chloroform/methanol=19/1-4/1), to provide 158 mg of the title compound as a colorless solid.

Aufarbeitung

  1. customThe reaction liquid
  2. washwashed successively with saturated aqueous sodium bicarbonate solution and saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resultant residue was purified by means of silica gel column chromatography (eluting solvent: chloroform/methanol=19/1-4/1)

Quellen und Nachweise

ORD-Eintrag
ord-1e93484a2b194065a30dcb7bf9e66e42
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809108B1

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