O-benzhydrylhydroxylamine → 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide

HRID 1872236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872236
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:11]1[C:28](O)=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[CH:42]([O:55][NH2:56])([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH:42]([O:55][NH:56][C:28]([CH:11]1[CH:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)(=[O:19])=[O:18])=[O:29])([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Komponenten

7

Edukt 4

HCID 198860O-benzhydrylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 186896293-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

Produkt 1

HCID 544390273-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-Benzyloxymethyl-1-(4-methoxybenzene sulfonyl)-azepane-2-carboxylic acid (19 mg, 0.044 mmoL) in 0.63 mL of dimethylformamide was added 1-Hydroxy-benzotriazole hydrate (7.1 mg, 0.0525 mmoL) and O-Benzhydryl-hydroxylamine (10.4 mg, 0.0525 mmoL). This solution was cooled to 0° C. and 1-(3-Dimethylamino propyl)-3-ethylcarbodiimide hydrochloride (10 mg, 0.0525 mmoL) was added in. The reaction was warmed to ambient temperature after 20 minutes, and the reaction was stopped after 3 hours by diluting with ethyl acetate. This solution was washed sequentially with saturated sodium bicarbonate, 0.5N HCl, and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by column chromatography (silica: 20% to 30% ethyl acetate in hexanes) to yield 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide; MS: (M+H)+ =615, (M+NH4)+ =632.

Aufarbeitung

  1. temperatureThe reaction was warmed to ambient temperature after 20 minutes
  2. washThis solution was washed sequentially with saturated sodium bicarbonate, 0.5N HCl, and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography (silica: 20% to 30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b3bc9c349d4846fdba08e5e9f620a8d5
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107291

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