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Hydrochloric Acid → methyl(2S,3R)-1-((S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-ylcarbamate

HRID 1751703
ノート
印刷プレビュー

反応式

HRID 1751703 の反応式
[Br:1][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14]C(C)(C)C)=O)=[N:4][CH:3]=1.Cl.[CH3:20][O:21][C@H:22]([CH3:32])[C@H:23]([NH:27][C:28]([O:30][CH3:31])=[O:29])C(O)=O.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.[Li+].[OH-]>C(Cl)Cl.CO.CN(C=O)C>[Br:1][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12](=[O:14])[C@@H:23]([NH:27][C:28](=[O:29])[O:30][CH3:31])[C@H:22]([O:21][CH3:20])[CH3:32])=[N:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 566051921,1-Dimethylethyl (2S)-2-(5-bromo-1H-imidazol-2-yl)-1-pyrrolidinecarboxylateHCID 59540170
(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

生成物 1

HCID 86688356methyl(2S,3R)-1-((S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-ylcarbamate収率 100%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

To a solution of (S)-tert-butyl 2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1.00 g, 3.2 mmol) in a mixture of CH2Cl2 (30 mL) and MeOH (5 mL) was added HCl (in dioxane, 4 M, 11.5 mL, 46.0 mmol). The solution was stirred at 40° C. for 1 h, cooled to room temperature, and concentrated to dryness under reduced pressure. To the crude intermediate suspended in CH2Cl2 (30 mL) was added (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (0.67 g, 3.5 mmol), HATU (1.47 g, 3.8 mmol), and DIPEA (1.00 mL, 6.0 mmol), The resulting solution was stirred at room temperature for 24 h. DMF (2 mL) and aqueous LiOH (2.5 M, 1 mL) were added and the reaction was concentrated to dryness under reduced pressure. The crude material was diluted with EtOAc and washed with H2O and brine. The aqueous layers were back extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (20% to 100% EtOAc (w/5% MeOH)/CH2Cl2) to afford methyl (2S,3R)-1-((S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-ylcarbamate (1.2 g, 100%).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness under reduced pressure
  3. stirringThe resulting solution was stirred at room temperature for 24 h
  4. concentrationthe reaction was concentrated to dryness under reduced pressure
  5. additionThe crude material was diluted with EtOAc
  6. washwashed with H2O and brine
  7. extractionThe aqueous layers were back extracted with EtOAc
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude residue was purified by silica column chromatography (20% to 100% EtOAc (w/5% MeOH)/CH2Cl2)

出典と根拠

ORDレコード
ord-38e2c953ddd54240addb796be644bc28
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156823B2

反応ノート

読み込み中…

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