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

HRID 1180412ノート

反応式

HRID 1180412 の反応式
ClC(Cl)(Cl)C(=N)O[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[C:22]([CH2:24][NH:25][C:26](=[O:33])[C@@H:27]([OH:32])[CH2:28][CH:29]([CH3:31])[CH3:30])#[N:23].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl.CCOC(C)=O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([CH:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[O:32][C@@H:27]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:26]([NH:25][CH2:24][C:22]#[N:23])=[O:33])=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 69472997(4-Bromophenyl)(cyclohexyl)methyl 2,2,2-trichloroethanimidoateHCID 86605382HCID 86605382、化合物

生成物 1

HCID 86605384(2S)-2-[(4-bromophenyl)(cyclohexyl)methoxy]-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 (4-bromophenyl)(cyclohexyl)methyl 2,2,2-trichloroethanimidoate of step 2 (4.18 mmol, 1.73 g) in CH2Cl2 (15 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide from Step 1, Example 67 (4.18 mmol, 0.71 g) and then PPTS (0.42 mmol, 0.105 g). The mixture was stirred at r.t. for 72 h. A red solution resulted. 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 gave the less polar diastereomer and the more polar isomer.

後処理

  1. customA red solution resulted
  2. washwashed with NaHCO3
  3. extractionThe organic extract
  4. dry with materialwas dried (anhyd. MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customChromatography gave the less polar diastereomer

出典と根拠

ORDレコード
ord-9ab3f52f40ba4e8289742f2622a924f6
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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