Phenylethanolamine → 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide

HRID 1951598ノート

反応式

HRID 1951598 の反応式
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:5].Cl.C(N=C=N)C.O.ON1C2C=CC=CC=2N=N1.[NH2:37][CH2:38][CH:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[OH:40].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:37][CH2:38][CH:39]([OH:40])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:13])=[CH:14][CH:15]=1)=[O:5]

参加物

8

反応物 5

HCID 1000PhenylethanolamineHCID 8471TriethylamineHCID 11329884-(2-Chlorobenzamido)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochloride

生成物 1

HCID 574653822-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide収率 80.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

under an N2 atmosphere, 4-(2-chlorobenzamido)benzoic acid (0.500 g, 1.81 mmol) was dissolved in N,N-dimethylformamide (10.0 ml) and the solution was treated with N-3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.696 g, 3.62 mmol), 1-hydroxybenzotriazole hydrate (0.491 g, 3.62 mmol), 2-amino-1-phenylethanol (0.498 g, 3.62 mmol), and triethylamine (0.506 ml, 3.62 mmol). The reaction was allowed to stir at room temperature overnight. The reaction was diluted with ethyl acetate and washed with 0.5N HCl followed by 5% NaHCO3. The organic layer was dried (Na2SO4), and concentrated in vacuo. The resulting solid was triturated with a mixture of ethyl acetate and hexanes to afford 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide (0.578 g, 71.5%) after collecting the solid by filtration. ESI m/z=395.0 (M+H+).

後処理

  1. washwashed with 0.5N HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was triturated with a mixture of ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-b503c0adfdb8422f8102b52e8cac45d9
出典データセット
uspto-grants-2013_03
特許番号
US08404722B2

反応ノート

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