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

HRID 1872236ノート

反応式

HRID 1872236 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b3bc9c349d4846fdba08e5e9f620a8d5
出典データセット
uspto-grants-2000_08
特許番号
US06107291

反応ノート

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