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

HRID 1180412Notes

Reaction equation

HRID 1180412 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9ab3f52f40ba4e8289742f2622a924f6
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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