Phenacylamine → (s)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-n-(2-oxo-2-phenyl-ethyl)-3-phenyl-propionamide

HRID 1524858노트

반응식

HRID 1524858 반응식
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:14])[C:9]([OH:11])=O)=[CH:3][CH:2]=1.[NH2:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1>[O:14]=[C:13]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:12]1[C@@H:8]([CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:9]([NH:23][CH2:24][C:25](=[O:26])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:11]

참가 물질

5

반응물 3

HCID 11952PhenacylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 334207(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acid

생성물 1

HCID 66674794(s)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-n-(2-oxo-2-phenyl-ethyl)-3-phenyl-propionamide수율 100%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

N-Phthaloyl-L-phenylalanine (290 mg, 1 mmol) and 2-aminoacetophenone (171 mg, 1 mmol) were dissolved in 10 mL of pyridine. Bop reagent (470 mg, 1.1 mmol) was added The mixture was stirred at rt under N2 for 12 h. The solvent was removed. The residue was dissolved in EtOAc and washed with water and sat. NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated to yield 412 mg of the product (100% yield). MS 413.2 (M+H)+.

후처리

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water and sat. NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5462f1e45a1944999ce18cfd03fc8b28
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079860B2

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