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

HRID 1951598노트

반응식

HRID 1951598 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-b503c0adfdb8422f8102b52e8cac45d9
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404722B2

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