Diisopropylethylamine → HCID 86688376, 화합물

HRID 1413021노트

반응식

HRID 1413021 반응식
[Br:1][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][C@H:10]([CH3:12])[CH2:9][N:8]2[C:13]([O:15]C(C)(C)C)=O)=[N:4][CH:3]=1.[CH3:20][O:21][C:22]([NH:24][C@@H:25]([C@@H:29]([CH3:32])[CH2:30][CH3:31])C(O)=O)=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>Cl.CCO.CN(C=O)C>[Br:1][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][C@H:10]([CH3:12])[CH2:9][N:8]2[C:13](=[O:15])[C@@H:25]([NH:24][C:22](=[O:23])[O:21][CH3:20])[C@@H:29]([CH3:32])[CH2:30][CH3:31])=[N:4][CH:3]=1

참가 물질

9

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28378062L-Isoleucine, N-(methoxycarbonyl)-HCID 69675472HCID 69675472, 화합물

생성물 1

HCID 86688376HCID 86688376, 화합물수율 1,786.5%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

(2S,4S)-tert-butyl 2-(5-bromo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate (100 mg, 0.13 mmol) in 1.25 N HCl in EtOH (15 mL) was heated to 50° C. for 3 h and then concentrated under reduced pressure. The crude residue was treated with (2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoic acid (625 mg, 3.30 mmol), HATU (1.05 g, 2.77 mmol) and DMF (10 mL), then DIPEA (1.33 mL, 7.62 mmol) was added dropwise. After 2 h, the mixture was poured into saturated aqueous NaHCO3 and then extracted with EtOAc. The organic phase was washed successively with 5% aqueous LiCl and Brine. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (30 to 90% of 10% MeOH/EtoAc to Hexanes) afforded methyl(2S,3 S)-1-((2S,4S)-2-(5-bromo-1H-imidazol-2-yl)-4-methylpyrrolidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate (932 mg, 81%).

후처리

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed successively with 5% aqueous LiCl and Brine
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica column chromatography (30 to 90% of 10% MeOH/EtoAc to Hexanes)

출처 및 근거

ORD 기록
ord-c6203c4eb5174b468728e2e04015b093
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921341B2

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