Methanesulfonic Acid → HCID 86594556, compound

HRID 1744089Notes

Reaction equation

HRID 1744089 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:36])[C@H:6]([CH2:32][CH:33]([CH3:35])[CH3:34])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)#[N:2].CS(O)(=O)=O>C1COCC1>[C:1]([CH2:3][NH:4][C:5](=[O:36])[C@H:6]([CH2:32][CH:33]([CH3:34])[CH3:35])[NH:7][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)#[N:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 86594555HCID 86594555, compound

Product 1

HCID 86594556HCID 86594556, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of N1-(cyanomethyl)-N2-[3-(4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl)isoxazol-4-yl]leucinamide (15.5 mg, 0.031 mmol) in THF (2 mL) was added 8 equivalents of methanesulfonic acid (10% solution in dichloromethane) over 28 h. The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with dichloromethane (3×). The organic phase was filtered through cotton and evaporated. Purification by flash chromatography (2% to 15% methanol/dichloromethane+0.5% ammonium hydroxide) gave 3.8 mg of N1-(cyanomethyl)-N2-[3-(4-piperazin-1-ylphenyl)isoxazol-4-yl]leucinamide. MS (+ESI): 397.4 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with aqueous NaHCO3 solution
  2. extractionextracted with dichloromethane (3×)
  3. filtrationThe organic phase was filtered through cotton
  4. customevaporated
  5. customPurification by flash chromatography (2% to 15% methanol/dichloromethane+0.5% ammonium hydroxide)

Sources & evidence

ORD record
ord-ee2176cb922b40f7895500a6c7017710
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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