Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-2-{[1-(4-bromophenyl)-2-methylprop-2-enyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

HRID 1180414ノート

反応式

HRID 1180414 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)[C:6]([CH3:8])=[CH2:7].[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])[C:6]([CH3:8])=[CH2:7])=[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 694696351-(4-Bromophenyl)-2-methylprop-2-enyl 2,2,2-trichloroethanimidoateHCID 86605382HCID 86605382、化合物

生成物 1

HCID 10045254(2S)-2-{[1-(4-bromophenyl)-2-methylprop-2-enyl]oxy}-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 1-(4-bromophenyl)-2-methylprop-2-enyl 2,2,2-trichloroethanimidoate of step 2 (0.81 mmol, 300 mg) in CH2Cl2 (6 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide from Step 1, Example 67 (0.81 mmol, 137 mg) and then PPTS (0.081 mmol, 20 mg). The mixture was stirred at r.t. for 72 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 (20 mg each).

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-2fcf829d65cf462cabf88461e84d00fe
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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