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

HRID 1180417노트

반응식

HRID 1180417 반응식
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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-be6cdaad36614c5db8f5c4dd536a64a9
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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