Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-2-[1-(4-bromophenyl)-2-methylpropoxy]-N-(cyanomethyl)-4-methylpentanamide

HRID 1180417ノート

反応式

HRID 1180417 の反応式
ClC(Cl)(Cl)C(=N)O[CH:5]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7].[C:19]([CH2:21][NH:22][C:23](=[O:30])[C@@H:24]([OH:29])[CH2:25][CH:26]([CH3:28])[CH3:27])#[N:20].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.CC(C)=O.CCOC(C)=O>C(Cl)Cl.CCOC(C)=O>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH:5]([O:29][C@@H:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[C:23]([NH:22][CH2:21][C:19]#[N:20])=[O:30])[CH:6]([CH3:8])[CH3:7])=[CH:10][CH:11]=1

参加物

7

反応物 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21584569Ethylacetate acetoneHCID 694708711-(4-Bromophenyl)-2-methylpropyl 2,2,2-trichloroethanimidoateHCID 86605382HCID 86605382、化合物

生成物 1

HCID 10407458(2S)-2-[1-(4-bromophenyl)-2-methylpropoxy]-N-(cyanomethyl)-4-methylpentanamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the 1-(4-bromophenyl)-2-methylpropyl 2,2,2-trichloroethanimidoate (2.6 mmol, 0.97 g) in CH2Cl2 (15 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide from Step 1, Example 67 (3.9 mmol, 0.66 g) and then PPTS (0.26 mmol, 65 mg). The mixture was stirred at r.t. for 20 h. The mixture was diluted with EtOAc and washed with NaHCO3. The organic extract was dried (anhyd. MgSO4) and concentrated under reduced pressure to give an oil. Chromatography (10% Acetone/EtOAc) gave 2 diastereomers.

後処理

  1. washwashed with NaHCO3
  2. extractionThe organic extract
  3. dry with materialwas dried (anhyd. MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil

出典と根拠

ORDレコード
ord-be6cdaad36614c5db8f5c4dd536a64a9
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

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