3-Aminopropionitrile → (S)-Tert-butyl 3-(3'-chlorobiphenyl-4-yl)-1-(2-cyanoethylamino)-1-oxopropan-2-ylcarbamate

HRID 333335ノート

反応式

HRID 333335 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=[N:31][CH2:32][CH2:33][CH2:34][N:35](C)C.Cl.C1C=CC2N(O)N=NC=2C=1.NCCC#N>C1COCC1>[Cl:26][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[C:10]([NH:35][CH2:34][CH2:33][C:32]#[N:31])=[O:11])=[CH:15][CH:16]=2)[CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 16473-AminopropionitrileHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58280562(S)-2-(Tert-butoxycarbonylamino)-3-(3'-chlorobiphenyl-4-yl)propanoic acid

生成物 1

HCID 68748130(S)-Tert-butyl 3-(3'-chlorobiphenyl-4-yl)-1-(2-cyanoethylamino)-1-oxopropan-2-ylcarbamate収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-(3′-chlorobiphenyl-4-yl)propanoic acid (1 g, 2.66 mmol) in THF (30 ml) at room temperature was added EDC.HCl (1.020 g, 5.32 mmol) and HOBT (0.815 g, 5.32 mmol). The reaction was stirred at room temperature for 10 minutes then was added 3-aminopropionitrile (0.389 ml, 5.32 mmol) and TEA (0.742 ml, 5.32 mmol). The reaction mixture was stirred at room temperature for overnight. The reaction mixture was quenched by brine and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 2 to 4% EtOH/DCM) and gave the title compound: 1.1 g (yield: 97%). LCMS (condition B): 428.2 (M+1); retention time=1.20 min.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for overnight
  2. customThe reaction mixture was quenched by brine
  3. extractionwas extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by flash chromatography (silica gel, 2 to 4% EtOH/DCM)

出典と根拠

ORDレコード
ord-015b635762bf4b78b754266078543213
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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