Sodium Bicarbonate → N-(cyanomethyl)-N2-[3-methyl-4-(4-piperazin-1-ylphenyl)isoxazol-5-yl]leucinamide

HRID 1744142Notes

Reaction equation

HRID 1744142 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:37])[C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[NH:7][C:8]1[O:12][N:11]=[C:10]([CH3:13])[C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)#[N:2].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([CH2:3][NH:4][C:5](=[O:37])[C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[NH:7][C:8]1[O:12][N:11]=[C:10]([CH3:13])[C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:18][CH:19]=1)#[N:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86594577N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinamide

Product 1

HCID 86594578N-(cyanomethyl)-N2-[3-methyl-4-(4-piperazin-1-ylphenyl)isoxazol-5-yl]leucinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinamide (210 mg, 0.411 mmol) in dry THF (0.5 mL) under dry nitrogen was gradually added a total of 5 equivalents of MesO3H (100 μL, 1.37 mmol) over a period of 3 hours in portions of 1–2 equivalents at a time and the reaction mixture was stirred overnight. Aqueous sat. NaHCO3 was added carefully and the product was extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90) to afford N-(cyanomethyl)-N2-[3-methyl-4-(4-piperazin-1-ylphenyl)isoxazol-5-yl]leucinamide. MS (−ESI): 409.7 [M−1]−.

Workup

  1. extractionthe product was extracted with EtOAc (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90)

Sources & evidence

ORD record
ord-ff21cf14aaf748d3809d664f6b13a747
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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