Methanesulfonic Acid → HCID 10136883, compound

HRID 1744060Notes

Reaction equation

HRID 1744060 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([CH2:3][NH:4][C:5](=[O:6])[C@@H:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86594554HCID 86594554, compound

Product 1

HCID 10136883HCID 10136883, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 4-(4′-{[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino]-methyl}[1,1′-biphenyl]-4-yl)-1-piperazinecarboxylate (85 mg, 0.164 mmol) in dry THF (5 mL) under dry nitrogen was gradually added a total of 8 equivalents of MeSO3H (total of 85 μL, 1.31 mmol) over a period of 2 days in portions of 1–2 equivalents at a time. Aqueous sat. NaHCO3 was added carefully and the product extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90) to afford (2S)-N-(cyanomethyl)-4-methyl-2-({[4′-(1-piperazinyl)[1,1′-biphenyl]-4-yl]methyl}amino)pentanamide. MS (+APCI): 420.3 [M+1]+.

Workup

  1. extractionthe product extracted with EtOAc (3×)
  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-77e21637727b49b4abfdeaf741b3b902
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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