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

HRID 1180412노트

반응식

HRID 1180412 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 86605384(2S)-2-[(4-bromophenyl)(cyclohexyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ab3f52f40ba4e8289742f2622a924f6
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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