Diisopropylethylamine → HCID 86688376、化合物

HRID 1413021ノート

反応式

HRID 1413021 の反応式
[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

参加物

9

反応物 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、化合物

生成物 1

HCID 86688376HCID 86688376、化合物収率 1,786.5%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c6203c4eb5174b468728e2e04015b093
出典データセット
uspto-grants-2014_12
特許番号
US08921341B2

反応ノート

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