Ammonium Chloride → HCID 86761860, compound

HRID 2096134Notes

Reaction equation

HRID 2096134 reaction equation
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)[CH2:3]CC.[CH2:19]([CH:26]1[N:31]([CH3:32])[C:30](=[O:33])[CH:29]([CH:34](C#C[Si](C)(C)C)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:28]([CH3:47])[C:27]1=[O:48])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH4+].[Cl-]>C1COCC1>[CH2:19]([CH:26]1[N:31]([CH3:32])[C:30](=[O:33])[CH:29]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:2]#[CH:3])[N:28]([CH3:47])[C:27]1=[O:48])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 68912754HCID 68912754, compound

Product 1

HCID 86761860HCID 86761860, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., tetrabutylammonium fluoride (1 mM in THF, 0.5 ml, 0.5 mmol) was added dropwise to 3-benzyl-1,4-dimethyl-6-(2-trimethylsilanylethynylbenzyl)piperazine-2,5-dione (140 mg, 0.22 mmol) in THF (abs., 5 ml). The mixture was stirred at this temperature for 1 h. After addition of NH4Cl solution (saturated, aq.), the mixture was extracted with ethyl acetate and the organic phases were dried and concentrated. Purification by column chromatography gave 50 mg (65%) of the target compound as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customthe organic phases were dried
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-faf56cd8982e43128d2385e44a6cc1bb
Source dataset
uspto-grants-2013_05
Patent number
US08450301B2

Reaction notes

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