Ethanolamine → N-[(S)-2-t-butoxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]-benzamide

HRID 646388ノート

反応式

HRID 646388 の反応式
[C:1]([O:5][CH2:6][C@H:7]([NH:11][C:12](=[O:34])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)[CH:14]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH:35][CH2:36][CH2:37][NH2:38].O.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:1]([O:5][CH2:6][C@H:7]([NH:11][C:12](=[O:34])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15](/[CH:21]=[CH:22]/[C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30]([F:31])([F:32])[F:33])=[CH:27][CH:28]=2)[CH:14]=1)[C:8](=[O:9])[NH:38][CH2:37][CH2:36][OH:35])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 700Ethanolamine2 回HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 27960291-Hydroxybenzotriazole hydrate2 回HCID 67002188(S)-3-t-butoxy-2-{4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoylamino}propionic acid

生成物 1

HCID 67001634N-[(S)-2-t-butoxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]-benzamide収率 76%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(S)-3-t-butoxy-2-{4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoylamino}propionic acid (25 mg), 2-hydroxyethylamine (9 μL), benzotriazol-1-ol monohydrate (19 mg), and (3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (25 mg) were dissolved in 2 mL of N,N-dimethylformamide, and then, N,N-diisopropylethyl-amine (53 μL) was added to the solution. The solution was stirred overnight at room temperature. Then, 2-hydroxyethylamine (9 μL), benzotriazol-1-ol monohydrate (19 mg), and (3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (25 mg) were added again to the solution, and the solution was further stirred overnight. After removal of the solvent under reduced pressure, to the obtained residue was added water, and the mixture was extracted three times with dichloromethane. The respective organic layers were combined, whereafter the combined organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and washed with dichloromethane. The filtrate and the washings were combined, and dichloromethane was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 44 mg (76%) of N-[(S)-2-t-butoxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]-benzamide.

後処理

  1. waitthe solution was further stirred overnight
  2. customAfter removal of the solvent under reduced pressure
  3. additionto the obtained residue was added water
  4. extractionthe mixture was extracted three times with dichloromethane
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe anhydrous sodium sulfate was separated by filtration
  8. washwashed with dichloromethane
  9. distillationdichloromethane was distilled off under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-2bbdde2affc441d285eb7e660ddaded2
出典データセット
uspto-grants-2010_04
特許番号
US07705053B2

反応ノート

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