Potassium bis(trimethylsilyl)amide → HCID 10917239, compound

HRID 634638Notes

Reaction equation

HRID 634638 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:39][CH3:40])=[C:16]([C:18]([C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=2[NH:30][C:31](=[O:38])[CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[O:19])[CH:17]=1>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:39][CH3:40])=[C:16]([C:18]2([OH:19])[C:20]3[C:21](=[CH:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=3)[NH:30][C:31](=[O:38])[CH:32]2[CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH:17]=1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 11762043HCID 11762043, compound

Product 1

HCID 10917239HCID 10917239, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 57 mL, 28.5 mmol) was added to a stirred cold (−78° C.) solution of 4-[[2-[(5-chloro-2-methoxyphenyl)carbonyl]-4-(trifluoromethyl)phenyl]amino]-4-oxobutanoic acid, methyl ester prepared in Step A (4.05 g, 9.1 mmol) in anhydrous THF (25 mL) and maintained at −78° C. for 3 hours. Acidic work-up with 1N HCl and followed by extraction with EtOAc afforded the crude title compound (4.05 g, 100%).

Workup

  1. extractionAcidic work-up with 1N HCl and followed by extraction with EtOAc

Sources & evidence

ORD record
ord-5fb52663fcce4f08968116445ac7f80c
Source dataset
uspto-grants-2001_02
Patent number
US06184231B2

Reaction notes

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