Imidazole → HCID 23439296, compound

HRID 1266660Notes

Reaction equation

HRID 1266660 reaction equation
[F:1][C:2]([CH3:34])([CH3:33])[CH2:3][CH2:4][CH:5]([CH2:9][CH:10]([OH:32])[CH:11]([NH:19][C:20]([C:22]1[CH:31]=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([OH:8])=[O:7].[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].N1C=CN=C1>CN(C)C=O>[C:38]([Si:35]([CH3:37])([CH3:36])[O:32][CH:10]([CH:11]([NH:19][C:20]([C:22]1[CH:31]=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH:5]([CH2:4][CH2:3][C:2]([F:1])([CH3:34])[CH3:33])[C:6]([OH:8])=[O:7])([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23439302HCID 23439302, compound

Product 1

HCID 23439296HCID 23439296, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-fluoro-3-methyl-butyl)-4-hydroxy-6-phenyl-5-[(quinoxaline-2-carbonyl)-amino]-hexanoic acid (1.63 g, 3.49 mmol) in dimethylformamide (10 mL) was added t-butyldimethylsilyl choride (3.2 g, 20.9 mmol) and imidazole (2.9 g, 41.9 mmol). The reaction was stirred for 4 days then quenched with methanol and stirred another 0.5 hours. The solution was diluted with ether and water. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated. Chromatography on silica gel gave the title compound (784 mg, 39%).

Workup

  1. customthen quenched with methanol
  2. stirringstirred another 0.5 hours
  3. additionThe solution was diluted with ether and water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0dcff6f7b2f74d9c85dd28623782809f
Source dataset
uspto-grants-2003_04
Patent number
US06548671B2

Reaction notes

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