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

HRID 1180417Notes

Reaction equation

HRID 1180417 reaction equation
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

Participants

7

Reactant 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, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-be6cdaad36614c5db8f5c4dd536a64a9
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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