Methanesulfonic Acid → HCID 22236104, compound

HRID 1744144Notes

Reaction equation

HRID 1744144 reaction equation
[C:1]([CH2:3][NH:4][C:5]([CH:7]([S:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26]C(=O)OC(C)(C)C)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][C:13]([S:12][CH:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:5]([NH:4][CH2:3][C:1]#[N:2])=[O:6])=[CH:14][CH:15]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86594579HCID 86594579, compound

Product 1

HCID 22236104HCID 22236104, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl {4′-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)thio]-1,1′-biphenyl-4-yl}methylcarbamate (1.75 g, 3.74 mmol) was dissolved in dioxane (15 mL). Methanesulfonic acid (485 μL, 7.5 mmol) was added and the reaction mixture was stirred for 18 h. Aqueous sat. NaHCO3 was added and the product was extracted with EtOAc (3×), dried over MgSO4, concentrated in vacuo, and purified by flash chromatography (95:3:2 dichloromethane/methanol/triethylamine) to yield 2-{[4′-(aminomethyl)-1,1′-biphenyl-4-yl]thio}-N-(cyanomethyl)-4-methylpentanamide.

Workup

  1. extractionthe product was extracted with EtOAc (3×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (95:3:2 dichloromethane/methanol/triethylamine)

Sources & evidence

ORD record
ord-21e0fe794dc142a68124cfa35ba11990
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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