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

HRID 558432노트

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HRID 558432 반응식
[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]

참가 물질

7

반응물 5

HCID 700Ethanolamine2회HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 27960291-Hydroxybenzotriazole hydrate2회HCID 67002188(S)-3-t-butoxy-2-{4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoylamino}propionic acid

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-38bc381fba2c4f8c8a00556d35f4b17f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063046B2

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